Chicago Travel Guide: 35 Things To Do In Chicago, Illinois, USA!

As a die hard Chicago Blackhawks and Cubs fan, sports is what first brought me to the Windy City. However, over the years – on subsequent visits – I’ve come to appreciate the phenomenal architecture, food scene, entertainment and cultural options the city has to offer. I was thrilled to be taking Audrey here for the first time.  Given that Chicago is my favorite city in North America, I felt an extra incentive to put forth my best effort with this travel video, photo essay and travel guide. The following is the city’s top attractions and underrated gems worth exploring:

35 Things to Do in Chicago Travel Guide

Here are some of the best things to do in Chicago:

source: Nomadic Samuel + That Backpacker via Samuel and Audrey on YouTube

1) Chicago Architecture and Chicago River Walk:

An ideal way to enjoy the architecture  in the downtown epicenter of Chicago is to take a river walk.

Chicago River is lined with impressive buildings on either side of the Chicago River providing you with ample opportunity to gawk at them.

Some of the architecture highlights included Marina City, Trump Tower, and The Wrigley & Tribune Building.  Although we did 35 things in the city, this was near the top of the list.

The city’s architectural journey began after the Great Chicago Fire of 1871, leading to a boom in building techniques and styles. From the historic Chicago Water Tower, one of the few structures to survive the fire, to the towering Willis Tower (formerly Sears Tower), Chicago showcases a stunning array of designs.

Walking through downtown, you’ll encounter architectural masterpieces like the John Hancock Center, known for its distinctive X-bracing exterior, and the Marina City Towers, iconic for their corncob-like appearance.

• Iconic Skyscrapers: Home to some of the world’s tallest and most recognizable buildings, including the Willis Tower and the Trump International Hotel and Tower.
• Architectural Tours: Guided tours provide in-depth knowledge and fascinating stories behind each structure, such as the renowned Chicago Architecture Foundation River Cruise.
• Diverse Styles: From Gothic Revival at the Tribune Tower to modernist designs like the Aqua Tower, there’s something for every taste.

Tip: Enhance your architectural exploration by downloading a self-guided tour map. This allows you to navigate the city at your own pace and discover hidden architectural gems you might otherwise miss.

2) Chicago River Boat Trip:

Alternatively, if you’re not up for a walk, architecture river tours are a thrilling way to take in the sights along the river.  You’ll notice boats of all shapes and sizes plying the Chicago River.

As you glide along the winding river, you’ll be treated to views of towering skyscrapers, historic bridges, and modern marvels that define Chicago’s unique landscape. The boat tours offer insightful commentary from knowledgeable guides who share fascinating stories and facts about the buildings and the city’s vibrant history. Thus, a riverboat trip  provides a fresh perspective and unforgettable memories.

• Guided Narratives: Expert guides provide engaging stories and historical insights about Chicago’s architecture and landmarks.
• Scenic Views: Enjoy panoramic vistas of the city’s skyline, including famous buildings like the Tribune Tower and Marina City.
• Variety of Tours: Choose from daytime sightseeing cruises, evening architectural tours, and specialized themed trips.

Tip: Book in advance to secure the best seats and ensure availability, especially during peak tourist seasons. Early reservations often come with perks like priority boarding and discounts.

3) Kayaking along the Chicago River:

If you find yourself here during the summer months kayaking is a popular activity – although, my goodness, I was sweating just looking at them on a day that was in the mid 30’s.

Heat issues aside, it’s a fantastic way to enjoy the outdoors while staying active and adventurous whilst exploring Chicago.

• Unique Perspectives: Experience Chicago’s skyline and bridges from the water, offering photo opportunities you won’t find elsewhere.
• Active Adventure: Get a full-body workout while enjoying the scenic beauty of the river and its surroundings.
• Eco-Friendly Travel: Kayaking is a sustainable way to explore the city without the noise and pollution of motorized boats.

Tip: Join a guided kayak tour if you’re new to the river. Guides can help you navigate the best routes and share interesting facts about the landmarks you pass.

4) Cloud Gate – The Bean:

Easily one of the most iconic structures in Chicago in recent years is the Cloud Gate also known as ‘The Bean.’  This unique marvel was the brainchild of Anish Kapoor.  Unless you visit before the crack of dawn, expect to be brushing elbows with other camera happy tourists.

While The Bean is visually captivating, its deeper meaning lies in its representation of liquid mercury and the fluid nature of city life. Kapoor’s intent was to create something that blurs the boundaries between reality and illusion. As you stand in front of the sculpture, you become part of the artwork, your image bending and curving with the reflective surface.

• Interactive Art: Encourages visitors to walk around and underneath for new visual perspectives.
• Iconic Reflection: The reflective surface offers stunning and surreal views of the skyline and surrounding area.
• Free Attraction: Located in Millennium Park, visiting The Bean is free and accessible to all.

Tip: Visit early in the morning or late at night to avoid large crowds and get the perfect photo of this iconic sculpture without interruptions.

5) Millennium Park:

The Crown Fountain is an interactive sculpture located in Millennium Park. It’s a nice escape from the stifling heat and you’ll encounter a throng of kids splashing around in the water.

Designed by Spanish artist Jaume Plensa, the fountain consists of two 50-foot glass towers that project videos of Chicago residents’ faces. At intervals, water pours from the mouths of the faces, creating a playful and refreshing environment, especially during hot summer days. It’s a perfect spot to cool off, splash around, and marvel at the creativity of the installation. The juxtaposition of digital art and natural elements makes the Crown Fountain a truly unique and fun part of the park’s offerings.

• Interactive Art: Water flows from the digital faces, inviting visitors, especially kids, to cool off and play.
• Digital and Physical Fusion: The installation blends modern video projections with the soothing sound of running water.
• Family-Friendly: A top spot for children to enjoy, especially on warm days when the fountain serves as an outdoor splash pad.

Tip: Wear comfortable, quick-dry clothing if you plan to spend time around the fountain, as you’re likely to get splashed while playing in the water.

6) Pavilion ‘Free Shows’

Summer is an ideal time to be in Chicago because of all the free events in the pavilion. We managed to catch a free movie and some concerts during our stay.  Remember this golden rule:  don’t forget your umbrella!

Its futuristic, flowing design, with a stainless-steel ribbon-like canopy, creates a striking contrast against the greenery of the park. The pavilion hosts free concerts and performances during the summer, including the Grant Park Music Festival, drawing crowds for everything from classical symphonies to jazz. The seating is free, with room for over 11,000 people. Both in the pavilion’s fixed seats and on the spacious lawn.

• Free Concerts: Enjoy live music ranging from classical to contemporary, with many free events throughout the year.
• Iconic Design: Frank Gehry’s signature architecture is a sight to behold, blending organic shapes with modern materials.
• Great Acoustics: The sound system is designed to create an immersive experience, even if you’re sitting on the lawn.

Tip: Bring a picnic blanket and some snacks to enjoy a relaxed evening of music under the stars on the pavilion’s expansive lawn.

7) Art Institute of Chicago:

Art lovers will enjoy the Art Institute of Chicago, which holds the work of Internationally renowned artists like Vincent Van Gogh and Paul Gaugin.  I’m not normally a huge fan of art galleries but this one is worth going to no matter whether you’re an art connoisseur or not.

As one of the oldest and largest art museums in the United States, it houses a diverse collection of over 300,000 works of art spanning multiple eras, styles, and cultures. From the iconic “American Gothic” by Grant Wood to the vivid, expressive brushstrokes of Van Gogh’s “The Bedroom”, the museum offers an impressive collection. As you explore its many galleries, you’ll find everything from ancient artifacts to modern art, with special exhibitions regularly enhancing the experience.

• Vast Collection: Home to over 300,000 works of art across various periods and mediums.
• Famous Masterpieces: See iconic works like Grant Wood’s American Gothic and Van Gogh’s The Bedroom.
• Special Exhibitions: Regularly rotating exhibits keep the experience fresh, featuring contemporary and historical art.

Tip: Plan at least 3–4 hours for your visit to fully appreciate the museum’s vast collection. If you’re short on time, grab a map and focus on the must-see galleries.

8) Watch a Chicago Cubs game at Wrigley Field:

Taking in a Chicago Cubs baseball game at Wrigley field is a must for anyone who visits the city.  Wrigley Field is a historic park featuring an ivy covered brick wall and hand operated outfield scoreboard.  You won’t find a ballpark quite like it anywhere else in the United States.  The Cubs, on the other hand, are affectionately called the ‘lovable losers’ having last won a World Series when the Ottoman Empire was still in existence.  They hold the rare distinction of being the most futile team in professional sports; however, that doesn’t stop the die hard fans (note: naive – myself included) from rooting for them.

Historic Ballpark

As the second-oldest ballpark in Major League Baseball, Wrigley Field has been home to the Cubs since 1914 and continues to charm fans with its classic ivy-covered outfield walls. Whether you’re a die-hard Cubs fan or just visiting the city, the energy in the stadium is contagious. From the seventh-inning stretch to the roar of the crowd after a home run, there’s nothing quite like a game day at Wrigley. Soak up the atmosphere. And be sure to grab a Chicago-style hot dog, as you enjoy America’s favorite pastime in one of the most beloved ballparks in the world.

• Historic Ballpark: Wrigley Field is a living piece of baseball history, beloved by fans for over a century.
• Game Day Atmosphere: The stadium buzzes with excitement from the moment you step inside, creating an electric environment.
• Cubs Tradition: From “Go Cubs Go” to the raising of the “W” flag after a win, Wrigley is rich in team tradition.

Tip: Arrive early to explore the ballpark, grab snacks, and check out the Wrigleyville neighborhood for pre-game excitement at the surrounding bars and restaurants.

9) Eat Deep Dish Pizza:

You can’t come to Chicago and not devour deep-dish pizza! During our week here we gormandized at many pizzerias in town including Lou Malnati’s, Giordano’s, Gino’s East Side, and Pizzeria Uno.  Picking a favorite would be tantamount to choosing a favorite child 😉

The buttery, flaky crust serves as the perfect foundation for layers of gooey mozzarella, savory toppings, and a rich tomato sauce that’s generously ladled on top. It’s pizza reimagined. Each bite feels like you’re diving into a warm, cheesy casserole.

• Buttery Crust: The foundation of deep dish, providing a rich, flavorful base that sets it apart from traditional pizza.
• Cheese Heaven: Layers of mozzarella create an oozy, decadent texture that’s irresistible.
• Toppings Galore: Whether you go classic with sausage or experiment with veggies and pepperoni, deep dish can handle it all.

Tip: Plan for extra time when ordering deep dish—it can take up to 45 minutes to bake to perfection. Use this time to enjoy appetizers or chat with friends!

What Makes Deep Dish Different

Deep dish pizza is a Chicago original. It’s very different from the thin, foldable slices you’ll find in New York. The crust is thick and almost pie-like, serving as a sturdy vessel for layers of cheese, sauce, and toppings. What truly sets it apart is the reverse layering—cheese goes directly on the crust, followed by toppings, and then it’s finished off with a rich, tangy tomato sauce. It’s a meal in itself. Just one slice can feel like a full meal. Thus, it’s perfect for sharing with friends or family.

• Pie-Like Crust: Thick, buttery, and flaky, the crust holds up to the weight of all the ingredients.
• Reverse Layering: Unlike traditional pizza, the cheese is placed under the toppings, creating a distinct texture and flavor.
• Hearty and Filling: Each slice is packed with cheese, sauce, and toppings, ensuring no one leaves hungry.

10) Visit the sky deck at Willis Tower (formerly Sears Tower):

Formerly known as the Sears Tower, Willis Tower is now the 2nd tallest building in the United States. It happened to be a foggy day when we visited ideally setting the scene for atmospheric photos.

Located on the 103rd floor of one of the tallest buildings in the Western Hemisphere. The Skydeck offers breathtaking panoramic views of the city and beyond. On a clear day, you can see up to four states—Illinois, Indiana, Michigan, and Wisconsin—making it one of the most impressive observation decks in the world. The real highlight of the visit is The Ledge. It’s a series of glass boxes extending 4.3 feet out from the side of the building.

• Stunning Views: On a clear day, take in panoramic views of Chicago, Lake Michigan, and even neighboring states.
• The Ledge: Step out onto glass boxes that extend over 1,300 feet above the ground for an unforgettable experience.
• One of the Tallest in the World: Willis Tower, once the tallest building in the world, is an architectural marvel that continues to captivate visitors.

Tip: Visit just before sunset to watch the city transition from day to night, when Chicago’s skyline begins to light up. It’s the best of both worlds.

11) Stroll around the University of Chicago campus:

The University of Chicago is one of the most gorgeous campuses I’ve ever had the privilege of setting foot on.  Gothic style buildings draped in Ivy are what you’ll notice as you meander you way around campus.  For a perfect example of this, step inside the beautiful Rockefeller Chapel.

Known for its Gothic Revival architecture, the campus is both picturesque and historically rich. You’ll instantly notice its ivy-covered buildings, tranquil courtyards, and tree-lined walkways. Famous landmarks like the Harper Memorial Library and the Robie House add to the campus’s allure. Hence, the University of Chicago campus offers a serene escape from the city’s hustle and bustle.

• Gothic Architecture: The university’s Gothic-style buildings are stunning examples of collegiate architecture.
• Beautiful Green Spaces: Courtyards and gardens provide peaceful places to relax and take in the scenery.
• Historic Landmarks: Harper Memorial Library and Robie House are must-see stops for any visitor.

Tip: Start your stroll at the main quadrangle, where many of the university’s most iconic buildings are located, for an easy and scenic introduction to the campus.

12) Check out the Oriental Institute of History:

The campus is also home to the Oriental Institute where the public can view an extensive collection of artifacts from the Ancient Near East.

One of the museum’s most famous artifacts is the Lamassu. It’s a massive winged bull with a human face, once used to guard the gates of ancient Assyrian cities. The Egyptian Gallery is another highlight, where you can marvel at well-preserved mummies and intricately carved statues of pharaohs and gods. Don’t miss the collection of cuneiform tablets, which offer a glimpse into the world’s earliest writing systems, documenting everything from trade transactions to poetry.

• Lamassu: A colossal winged bull statue from ancient Assyria, guarding the entrance to the galleries.
• Egyptian Gallery: Home to mummies, sarcophagi, and statues that transport you to ancient Egypt.
• Cuneiform Tablets: See the world’s first writing system up close, used by ancient Sumerians for thousands of years.

Tip: Take your time in the Egyptian Gallery—it’s one of the museum’s largest collections, and the details in the statues and artifacts are worth a closer look.

13) Marvel and escape the bustle at Osaka Garden:

Although Chicago is not nearly as chaotic as New York City, it can nevertheless be overwhelming at times.  I suggest visiting Osaka Garden to escape it all.  Located in Jackson Park, it is a tranquil place with lots of little paths that you can walk down.

Originally created in 1893 for the World’s Columbian Exposition, the garden was a gift from Japan to the people of Chicago. As you walk along the stone paths, you’ll cross a traditional Japanese bridge that arches gracefully over the reflective pond. Stone lanterns and benches dot the trail, giving you the perfect spot to sit and take in the serenity of the garden. The variety of trees, flowers, and plants—carefully pruned and arranged—enhance the garden’s peaceful ambiance.

• Japanese Bridge: A graceful red bridge that offers scenic views of the garden’s ponds and greenery.
• Stone Lanterns: Traditional lanterns add to the cultural authenticity of the garden, offering picturesque photo opportunities.
• Quiet Corners: Benches and secluded spots invite visitors to pause and reflect, surrounded by the beauty of nature.

Tip: Bring a book or journal and spend some time in one of the garden’s quiet corners. It’s the perfect spot for reading, writing, or simply reflecting.

14) Enjoy an afternoon or evening at Wicker Park:

This Chicago neighborhood was put on the map by the movie Wicker Park starring Josh Hartnett and Diane Kruger. If you visit the neighborhood today you’ll find it has a hipster feel, with lots of street art down every alley.

Located on the city’s northwest side, this eclectic area is known for its quirky shops, cool cafes, and an ever-changing street art scene. As you wander through its streets, you’ll find a blend of independent boutiques, vintage stores, and local eateries that reflect the neighborhood’s creative and diverse spirit.

• Independent Boutiques: Shop at unique, local stores offering everything from handmade jewelry to vintage clothing.
• Street Art: Admire colorful murals and street art scattered throughout the neighborhood.
• Cafes and Eateries: Enjoy a wide range of culinary delights, from laid-back brunch spots to trendy dining destinations.

Tip: Start your visit with a walk around the park itself—Wicker Park is a great green space for a relaxed stroll or a quick break before diving into the neighborhood’s offerings.

15) Relax and escape at Humboldt Park:

Humboldt Park is a little far removed from the downtown area so it’s not as popular with visitors, however, it’s an ideal location to soak in nature. You can wander around the pond, catch a pick up game of baseball, or grab a quick bite from one of the many food trucks parked in the area.

This 200-acre park, located in the West Side neighborhood, is a place where you can relax, unwind, and connect with nature. Known for its stunning lagoons, wide-open green spaces, and historic boathouse, Humboldt Park feels like a mini-retreat in the heart of the city. Whether you’re out for a leisurely walk, taking a paddleboat ride, or enjoying a picnic on the grass, the park’s tranquil atmosphere makes it easy to forget about the urban hustle. It’s a spot to breathe in fresh air and slow down.

• Beautiful Lagoons: Two scenic lagoons offer the perfect backdrop for walking, boating, or just relaxing by the water.
• Wide Open Spaces: Plenty of room for picnics, frisbee games, or simply lying in the grass.
• Historic Boathouse: A picturesque structure that adds charm and provides a peaceful spot to sit and enjoy the view.

Tip: Visit on a weekday morning for a quieter experience when the park is at its most peaceful, allowing you to enjoy the serenity uninterrupted.

16) Check out the Dinosaur exhibits at the Chicago Field Museum:

For a chance to lock eyes with dinosaurs, head over to the Field Museum. This museum is home to the largest and most complete T-Rex to have ever been found and her name is Sue.  Ain’t she pretty?

The museum’s dinosaur exhibits are among the most impressive in the world, with the star attraction being SUE the T. rex. It’s the largest and most complete Tyrannosaurus rex skeleton ever discovered. As you walk into the exhibit, you’ll be greeted by SUE’s towering frame, giving you a sense of the sheer size and power these ancient creatures once had. The exhibit goes beyond just bones. Interactive displays teach you about SUE’s life, diet, and the world she lived in.

• SUE the T. rex: The largest and most complete T. rex skeleton ever found.
• Interactive Displays: Learn about SUE’s life, hunting techniques, and even her injuries.
• Impressive Size: Standing 13 feet tall at the hips, SUE is a must-see for any visitor.

Tip: Visit early in the day to avoid the crowds and spend more time with SUE, especially during peak tourist seasons.

17) Visit the Shedd Aquarium – the largest indoor one in the world:

Right next door is the Shedd Aquarium which is a popular attraction for families.  We enjoyed checking out the plethora of museums in this surrounding area to kill time on a rainy day.

Located along the shoreline of Lake Michigan, it’s the largest indoor aquarium in the world. It’s home to more than 32,000 animals from oceans, rivers, lakes, and reefs. From sharks and dolphins to sea turtles and jellyfish, Shedd’s expansive exhibits let you explore marine life up close. You’ll encounter immersive habitats that make you feel like you’re underwater.

• 32,000 Animals: See marine life from oceans, lakes, rivers, and reefs all in one place.
• Immersive Habitats: Exhibits make you feel like you’re stepping into an underwater world.
• Stunning Location: Located right on Lake Michigan, offering beautiful views before or after your visit.

Tip: Plan ahead and purchase your tickets online to avoid the long lines, especially during weekends and school holidays.

18) Watch a Chicago Blackhawks game at the United Center:

My beloved Chicago Blackhawks!  As a Canadian, hockey is my religion of choice.  If the Cubs have been the ultimate failure of a franchise, the Blackhawks have more than made up for it with Stanley Cup victories in 2010 and 2013.  One day I’d like to see a Jonathan Towers and Patrick Kane statue next to the Bobby Hull (pictured above) one.

As one of the Original Six NHL teams, the Blackhawks have a rich history that comes alive every time they hit the ice. The United Center, affectionately known as the Madhouse on Madison, lives up to its nickname on game nights. The fans are some of the most passionate in the NHL. During iconic moments like the national anthem, the crowd cheers loudly from start to finish. The tradition dates back decades and gives you goosebumps every time.

• Loud and Proud: The national anthem at a Blackhawks game is an experience you don’t want to miss.
• Tommy Hawk: The team mascot keeps the energy high, engaging with fans throughout the game.
• Fan Traditions: From goal celebrations to in-game chants, Blackhawks fans know how to make the game exciting.

Tip: Join in on the chants and cheers—it’s all part of the fun, and being part of the crowd’s energy makes the game even more memorable.

19) Check out the ‘Borders’ exhibit at Solti Gardens of Grant Park:

While in the city, we also got to visit an art installation called “Borders”. It’s located in the Solti Gardens at Grant Park and I dare you not to have fun trying to blend in with the sculptures 😉

The exhibit features large-scale sculptures that explore the concept of borders—physical, emotional, and political—and how they shape our lives and societies. As you wander through the garden, you’ll encounter these thought-provoking installations, each one encouraging reflection on the invisible lines that divide and connect us. The peaceful setting of Solti Gardens, with its manicured greenery and quiet pathways, provides the perfect backdrop for such a contemplative exhibit.

• Thought-Provoking Art: Sculptures that explore the concept of borders and how they impact our world.
• Scenic Setting: Solti Gardens provides a tranquil, natural environment to reflect on the art.
• Engaging Experience: The exhibit encourages visitors to think critically about boundaries, division, and unity.

Tip: Visit during the early morning for a more peaceful and private experience, allowing you to fully immerse yourself in the art and surroundings.

20) Admire Buckingham Fountain during the day or at night:

Most spectacular at night, Buckingham Fountain was used in the 90’s sitcom Married with Children during the opening credits.

Located in Grant Park, the fountain is one of the largest in the world and serves as a stunning centerpiece against the city’s skyline. By day, the fountain’s graceful water jets sparkle in the sunlight, with the sound of water providing a calming backdrop to the bustling park. At night, Buckingham Fountain transforms into a magical display. Its colorful lights and synchronized water shows create a mesmerizing atmosphere.

• Daytime Beauty: See the fountain’s intricate details and enjoy the peaceful sound of cascading water.
• Nighttime Magic: At night, the fountain comes alive with a stunning light and water show.
• Perfect Photo Spot: Capture the beauty of the fountain with the city skyline in the background.

Tip: Visit at dusk to catch the transition from day to night—watch as the lights slowly illuminate the fountain, creating a breathtaking scene.

21) View the Chicago skyline from the Hancock Center:

Having already gone up the Willis Tower by day, we decided to visit the John Hancock Center by night. The city really dazzles from the 94th floor and -boy oh boy – is Chicago ever pretty when the lights shine at night.

Located on the 94th floor, this viewing platform offers unparalleled, 360-degree views of the city, Lake Michigan, and beyond. Whether you’re visiting during the day to see the city’s iconic skyscrapers stretching into the sky or at night when the entire skyline is illuminated, the Hancock Center delivers an unforgettable experience. The deck’s floor-to-ceiling windows provide a crystal-clear view. It allows you to spot landmarks like Navy Pier, Millennium Park, and even neighboring states on a clear day.

• 360-Degree Views: Enjoy panoramic sights of the entire city and Lake Michigan.
• Iconic Landmarks: Spot famous Chicago landmarks like Navy Pier and Millennium Park from high above.
• Day or Night: Both daytime and nighttime offer unique and stunning perspectives of the skyline.

Tip: Visit just before sunset to witness the transition from day to night—watching the city light up as the sun goes down is magical.

22) Spend an afternoon having fun at Navy Pier:

The Navy Pier is a fun place to visit on a weekend as a family outing or for date night. The pier is lined with fun rides including a giant Ferris Wheel, a wave swing, and a carousel.

Spending an afternoon at Navy Pier is one of the best ways to enjoy the heart of Chicago’s lakefront. As you stroll along the pier, you’ll be greeted by the lively sounds of street performers, the aroma of delicious food, and the vibrant energy of tourists and locals alike. Whether you’re hopping on a lakefront cruise, riding the Centennial Wheel, or simply relaxing by the water, Navy Pier provides the perfect backdrop for a fun and memorable day. It’s no wonder this spot is one of Chicago’s top attractions year-round.

• Family Fun: Navy Pier is packed with attractions like the Centennial Wheel and Chicago Children’s Museum.
• Scenic Lakefront Views: Enjoy panoramic views of Lake Michigan as you walk along the pier.
• Entertainment Galore: From live performances to fireworks shows, Navy Pier always has something happening.

Tip: Visit during the week for smaller crowds, especially if you’re looking for a more relaxed experience away from the weekend rush.

23) Wander around Lincoln Park Zoo and Conservatory:

There are a number of free attractions in Chicago. One of them being the Lincoln Park Zoo. While visiting we spotted plenty of animals including polar bears, lions, tigers, and rhinos. Afterwards we headed over to conservatory which is worth a peak.

The zoo is home to a wide variety of animals, from majestic lions and playful otters to exotic birds and curious reptiles. As you wander the zoo’s beautifully landscaped grounds, you’ll encounter immersive exhibits that bring you up close to creatures from around the world. Whether you’re visiting with family or just looking for a relaxing day outdoors, Lincoln Park Zoo offers an escape from the hustle and bustle of city life.

• Free Admission: One of the few remaining zoos in the U.S. that doesn’t charge an entry fee.
• Wide Variety of Animals: Lions, giraffes, primates, and more call the zoo home.
• Family-Friendly: With exhibits for all ages, it’s an enjoyable day out for visitors young and old.

Tip: Visit during weekdays for a quieter experience, especially in the morning when the animals are most active.

24) Work out or get a tan at North Avenue Beach:

Located in the north end of the city, North Avenue Beach is a popular hangout spot with beach-dwellers. You’ll find people jogging, playing sports, and working on their tans.

Located along the stunning shoreline of Lake Michigan, this beach offers plenty of space for outdoor activities, whether you want to get a serious workout in or just relax and catch some rays. With volleyball courts, running and biking paths, and an outdoor gym, it’s easy to stay active while enjoying the scenic views. If working out isn’t on your agenda, grab a spot on the sand and spend the afternoon tanning, reading a book, or dipping your toes in the lake.

• Fitness Hub: Enjoy the outdoor gym, volleyball courts, and scenic running and biking paths.
• Sun and Sand: Lay out a towel, soak up the sun, or take a dip in Lake Michigan’s cool waters.
• Beautiful Views: The lakefront provides panoramic views of the water and the city skyline.

Tip: Arrive early to secure a prime spot on the sand, especially during peak summer weekends.

25) Laugh your head off watching improv at The Second City:

For improvise comedy there’s no better place than The Second City. This theater troupe has seen some pretty big names wander through its halls over the decades.

This iconic comedy club is where some of the biggest names in comedy—like Tina Fey, Steve Carell, and Bill Murray—got their start. The atmosphere is always electric, with talented comedians delivering fast-paced, witty performances that leave the audience in stitches. No two shows are ever the same. Moreover, the cast creates sketches and scenes on the spot based on audience suggestions.

• Comedy Legends: The Second City has been the launching pad for comedy icons like Tina Fey and Bill Murray.
• Unpredictable Fun: Every show is different, making each visit a unique experience.
• Audience Participation: Audience suggestions fuel the hilarious scenes and sketches.

Tip: Buy tickets in advance—shows often sell out, especially on weekends, so plan ahead to snag your spot.

26) Test your mind playing the Zombie Game:

Audrey’s new obsession.  These mind maze games are a real trip.  We come close to solving this one but ultimately ran out of time.  The result?  We were eaten by Zombies 😉

This interactive, real-life escape room game plunges you into a thrilling scenario where you must outsmart zombies and escape before time runs out. The premise is simple: you and your team are trapped in a room, and there’s a zombie chained to the wall. Every five minutes, the chain gets a little longer, bringing the zombie closer. To escape, you’ll need to work together to solve puzzles, find hidden clues, and unlock the door before the zombie reaches you.

• Real-Life Escape Room: Work with your team to solve puzzles and unlock the door before time runs out.
• Zombie Challenge: Every few minutes, the zombie gets closer, adding to the tension and excitement.
• Teamwork Required: You’ll need to collaborate and communicate with your team to survive the game.

Tip: Form a team with a variety of strengths—having different perspectives and skills will help you solve the puzzles more quickly.

27) Go shopping or people watching along the Magnificent Mile:

The Magnificent Mile is a shopper’s paradise. This area is home to high end boutiques and department stores.  If you don’t have a fat wallet come to people watch instead.

Whether you’re hunting for designer pieces or simply window shopping, there’s something for every style and budget. With stunning architecture and lively streets, it’s easy to spend an entire afternoon here without even stepping foot inside a store.

• High-End Boutiques: Shop at designer stores like Gucci, Louis Vuitton, and Tiffany & Co.
• Department Store Icons: Visit famous names like Nordstrom and Macy’s, all within walking distance.
• People-Watching Paradise: Watch the world go by as locals, tourists, and street performers make their way through the busy avenue.

Tip: Take a break at a sidewalk café—it’s the perfect spot to sit back, sip a coffee, and enjoy the lively atmosphere.

28) Take the Chicago ‘El or ‘L’ CTA metro system:

The Chicago L, or the elevated line, is tailor made for zipping around town. A week pass is $28 for unlimited travel.  This is the best value purchase you’ll make during your week long stay in the Windy City.

Hopping on the ‘L’ is one of the best ways to get around the city quickly and affordably. The iconic elevated tracks, which snake through Chicago’s neighborhoods and downtown, offer a unique vantage point of the city’s architecture and skyline. With eight different color-coded lines, the ‘L’ can take you almost anywhere—from popular tourist attractions like the Loop and Wrigley Field, to the more local hotspots in neighborhoods like Logan Square and Hyde Park. It’s a quintessential part of Chicago life. Moreover, it’s a great way to experience the city like a local.

• Fast and Affordable: The ‘L’ is an efficient and budget-friendly way to travel across Chicago.
• Great Views: Elevated tracks offer unique perspectives of the city’s skyline and architecture.
• Comprehensive Coverage: With multiple lines, you can reach most neighborhoods and attractions easily.

Tip: Get a Ventra card for easy access—this reloadable transit card makes hopping on and off the ‘L’ simple and hassle-free.

29) Watch an NFL football game (Chicago Bears) at Soldier Field:

Da Bears!  For NFL football action check out a Chicago Bears game at Soldier Field.  They play in the fall/winter months.

As one of the oldest stadiums in the NFL, Soldier Field has been home to the Bears since 1971 and offers a classic, gritty atmosphere for football fans. The energy inside the stadium is infectious! The moment you step inside, you’ll feel the excitement building as fans don their orange and navy, ready to cheer on their team. With the backdrop of Lake Michigan and the Chicago skyline, Soldier Field is more than just a sports venue. It’s a place where the city’s passion for football comes alive.

• Historic Stadium: Soldier Field is one of the NFL’s oldest and most iconic stadiums.
• Electric Atmosphere: The fans are loud, proud, and passionate, making every game an unforgettable experience.
• Scenic Location: The stadium’s position by Lake Michigan provides stunning views and a one-of-a-kind backdrop for the game.

Tip: Arrive early to explore the stadium and take in the pre-game festivities—tailgating at Soldier Field is an event in itself!

30) Check out the entirely free Money Museum:

Notice above that shiny two dollar bill with a rather distinct (yet familiar) looking face 😉  As another one of Chicago’s many free attractions, I’d recommend visiting the under-rated Money Museum at the Federal Reserve Bank of Chicago.  We were the only ones there when we went!

If you’ve ever wondered what $1 million in cash looks like, then a visit to the Money Museum is a must. The exhibits are engaging and educational, with plenty of hands-on displays that allow you to explore everything from how money is made to how inflation affects purchasing power. One of the highlights is the chance to take a photo with a briefcase holding $1 million in real currency—an Instagram-worthy moment for sure!

• Free Admission: The Money Museum is completely free to visit, making it an accessible activity for all.
• Interactive Exhibits: Learn about the economy, the history of currency, and how the Federal Reserve works through hands-on displays.
• $1 Million Display: Get up close and personal with a briefcase filled with $1 million in real cash.

Tip: Visit on a weekday when the museum is less crowded, giving you more time to explore the exhibits at your own pace.

31) Ride a bicycle in downtown Chicago:

The Divvy is Chicago’s bike sharing system. It is ideal for quick trips and you can drop the bikes off at any station around town.  This is what you’ll want to be doing after stuffing your face with deep dish pizza 😉

With a network of dedicated bike lanes, you can safely navigate through the heart of the city while soaking in iconic views of landmarks like the Willis Tower, Millennium Park, and the Chicago Riverwalk. Whether you’re commuting, sightseeing, or just enjoying a leisurely ride, cycling downtown gives you a different perspective of the city’s bustling energy. Plus, with Chicago’s Divvy bike-sharing program, it’s easy to grab a bike and go without any hassle. It’s an eco-friendly, fun, and active way to explore everything the Windy City has to offer.

• Bike-Friendly City: Chicago boasts a network of bike lanes, making it easy and safe to navigate the downtown area.
• Divvy Bike Share: Grab a bike anytime with Divvy, the city’s convenient bike-sharing system.
• Iconic Sights: Cycling lets you see the city’s famous landmarks up close, from the Chicago River to Millennium Park.

Tip: Download the Divvy app to locate nearby docking stations and check bike availability, making your ride even more seamless.

32) Spend time at the Museum of Science and Technology:

Chicago’s Museum of Science and Technology is the largest science museum in the Western Hemisphere. They cover everything from submarines to weather patterns.

With over 400,000 square feet of exhibits, this museum is perfect for both kids and adults looking to learn in a hands-on, interactive way. From the famous U-505 submarine to immersive displays about space exploration and robotics, MSI brings science to life in a way that’s both fun and educational. You can easily spend an entire day wandering through the fascinating exhibits, discovering how science shapes the world around us.

• Interactive Exhibits: Hands-on experiences make learning about science engaging for all ages.
• Massive Space: With over 400,000 square feet, there’s always something new to explore.
• U-505 Submarine: Get up close and personal with this historic World War II submarine.

Tip: Arrive early to give yourself plenty of time to explore the exhibits, as the museum is large and packed with fascinating content.

33) Visit Robbie House:

This home may not look that impressive from the exterior, but it’s an important example of the Prairie School architectural style which is uniquely American.

Designed by the legendary Frank Lloyd Wright, this house is a stunning example of the Prairie School style, which emphasizes horizontal lines, flat roofs, and a connection to the natural surroundings. Located in the Hyde Park neighborhood, Robie House has been preserved as a National Historic Landmark and is widely considered one of Wright’s most important works. As you walk through the house, you’ll notice Wright’s genius in every detail, from the custom-designed furniture to the flowing, open spaces that seamlessly connect the indoors with the outdoors.

• Prairie School Architecture: Frank Lloyd Wright’s signature style emphasizes horizontal lines and natural materials.
• Historic Landmark: Robie House is recognized as a National Historic Landmark for its groundbreaking design.
• Integrated Design: Everything in the house, from the windows to the furniture, was carefully designed by Wright to create a unified aesthetic.

Tip: Book your tour in advance to ensure a spot, as tours often fill up quickly, especially on weekends.

34) Rest your legs by taking a Chicago city tour by Segway:

If you tire of walking, segway tours are a zestful way to zip around the city.

This unique experience lets you cover more ground than walking, all while effortlessly cruising along on two wheels. Whether you’re new to Segways or a seasoned pro, the tours are designed for all skill levels, making it an easy and enjoyable ride for everyone. From the lakefront views of Navy Pier to the lush greenery of Grant Park, a Segway tour allows you to explore the city’s highlights while giving your legs a well-deserved break.

• Effortless Exploration: Cover more ground than walking while enjoying a relaxed, smooth ride.
• Iconic Landmarks: See major sites like Navy Pier, Grant Park, and Buckingham Fountain up close.
• Perfect for All Levels: Whether it’s your first time or you’re a pro, Segway tours are beginner-friendly and fun for everyone.

Tip: Wear comfortable shoes—while you won’t be walking much, standing on the Segway for extended periods can still tire your feet.

35) Check out a performance at Chicago Theatre:

It’s hard to miss the flashing lights of the historic Chicago Theatre! Their events calendar is packed with some big names from the music industry.

With its famous marquee lighting up State Street, the theater has been a staple of Chicago’s cultural scene since 1921. The architecture, including its grand lobby and intricate details, gives you a glimpse into the golden age of cinema and live entertainment. From Broadway shows to concerts and comedy acts, the Chicago Theatre hosts a wide variety of performances throughout the year.

• Historic Venue: The Chicago Theatre has been a beloved part of the city’s cultural fabric for over a century.
• Diverse Performances: You can see everything from musicals to stand-up comedy at this renowned venue.
• Stunning Architecture: The theater’s ornate design is a visual treat in itself, making your night out even more special.

Tip: Arrive early to snap a photo under the iconic marquee before heading inside—it’s one of Chicago’s most photographed landmarks.

Planning Your Chicago Trip: Beyond the 35 Things To Do

You’ve got the big list of cool things to do in Chicago. Now let’s turn that into an actual trip you can map out day by day without feeling overwhelmed, broke, or frozen solid by lake winds.

This is where we zoom out a bit: where to stay, how long to come for, how to get around, when to visit, and how to string all those attractions into a proper Windy City adventure.

How Many Days Do You Need in Chicago?

You can technically blast through Chicago in a day or two, but the city really comes alive when you slow down a little. Think in terms of how many “themes” you want: architecture, museums, sports, parks, food, neighbourhoods.

2 Days in Chicago: First-Time Highlights

If you’ve only got a weekend, focus on the greatest hits clustered downtown and along the lake:

• Architecture river cruise or riverwalk
• Millennium Park & The Bean
• Art Institute of Chicago
• Willis Tower or Hancock Center for views
• Deep dish pizza meal
• Evening at Navy Pier or The Second City

A simple 2-day flow could look like:

Day 1 (Downtown & Architecture)

• Morning: Architecture river cruise or self-guided riverwalk
• Midday: Millennium Park (Bean, Crown Fountain)
• Afternoon: Art Institute
• Evening: Deep dish pizza + stroll the Chicago Riverwalk lit up at night

Day 2 (Views & Lakefront Fun)

• Morning: Willis Tower or Hancock Center
• Midday: Lunch + Magnificent Mile wander
• Afternoon: Navy Pier
• Evening: Improv at The Second City

You won’t see everything, but you’ll leave with a good sense of the city’s look and feel.

3–4 Days: The “This City Is Awesome” Trip

With 3–4 days, you can add neighbourhoods and museums without racing around:

• All the 2-day highlights
• One serious museum day (Field Museum + Shedd, or Museum of Science and Industry)
• An afternoon in Wicker Park or Logan Square for food and street art
• A game day if your dates line up (Cubs, Blackhawks, Bears)
• Time at the beach (summer) or extra indoor attractions (winter)

5+ Days: Settle In Like a Temporary Local

Five or more days is where Chicago really hooks you:

• Slow mornings in neighbourhood cafés
• Multiple sports events or live shows
• Day trip style explorations: Hyde Park & University of Chicago, Osaka Garden, Robie House
• Repeat visits to favourite spots (yes, that includes more deep dish)

At that point you’re not just “visiting Chicago” — you’re flirting with the idea of moving there.

Where to Stay in Chicago: Neighbourhood Breakdown

Chicago is very much a neighbourhood city. Where you stay changes the feel of the trip just as much as what you do.

Best Areas to Base Yourself

Here’s a quick comparison to help you pick your home base:

Picking Based on Your Trip Style

• First Visit, Want It Easy: Loop, River North, or Magnificent Mile. You’ll walk a ton and barely touch transit beyond the airport and a few ‘L’ rides.
• Food & Nightlife Trip: River North or Wicker Park/Bucktown. Think late-night tacos, craft beer, and street art.
• Family Trip: Lincoln Park or the Loop. Lincoln Park gives you parks + zoo; the Loop gives you easy transit to everything else.
• Return Visit / Slower Pace: Hyde Park or Wicker Park/Bucktown for a more local, less touristy feel.

Getting Around Chicago Without Losing Your Mind (or Budget)

You’ve got options: CTA ‘L’ trains, buses, Divvy bikes, rideshares, walking, and even water taxis in season. The city is big, but it’s not unmanageable.

CTA ‘L’ and Buses

The CTA is your backbone: it’ll take you from the airport into the city and out to most of the places in the original list of 35 things to do.

• O’Hare → Downtown: Blue Line
• Midway → Downtown: Orange Line
• Wrigley Field: Red Line
• Hyde Park / Museum of Science & Industry: combo of Metra Electric + buses or CTA buses from downtown

Multi-day passes are often the best deal if you’re riding several times a day. Pay once, then stop thinking about exact fares and transfers.

Bikes, Walking & Water

• Divvy Bikes: Perfect for short hops along the lakefront or for connecting between neighbourhoods on nice days.
• Lakefront Trail: If the weather cooperates, walking or biking this stretch is a highlight in itself — think beaches, skyline views, people-watching for days.
• Water Taxis (seasonal): Handy and fun between places like Navy Pier, Michigan Avenue, and Chinatown. It’s transport that doubles as a mini-sightseeing cruise.

Transit vs Rideshare vs Walking: Quick Decision Matrix

If you hate the idea of constantly watching the meter, load up a transit pass and let the ‘L’ and buses do the heavy lifting.

Eating & Drinking in Chicago: Beyond Deep Dish

Let’s be serious. Deep dish has already stolen the show. But Chicago’s food scene goes far beyond one style of pizza.

Classic Chicago Bites to Hunt Down

You don’t have to eat everything in one day (your stomach will riot), but try to tick off a few of these:

• Chicago-Style Hot Dog:
  All-beef dog, poppy seed bun, mustard, onions, relish, tomato, sport peppers, pickle spear, celery salt.
  Rule #1: no ketchup. Ever.
• Italian Beef Sandwich:
  Thinly sliced roast beef piled into a long roll, dipped in jus, topped with sweet peppers or spicy giardiniera.
  Order it “wet” or “dipped” if you’re not afraid of a messy, glorious sandwich.
• Tavern-Style Pizza:
  Deep dish gets all the hype, but locals crush thin, crispy tavern-style pizza cut into small squares. Perfect bar food, especially with a beer.
• Garrett-Style Popcorn Mix:
  Sweet + salty caramel and cheese popcorn mix. Addictive. Excellent train snack. Dangerous to keep in arm’s reach.
• Mexican & Latin American Food:
  Chicago’s Mexican food is superb. If you have time, explore neighbourhoods with strong Mexican communities and eat your way through tacos, tortas, and tamales.

When to Splurge vs Keep It Simple

You don’t need every meal to be a destination restaurant. Mix it up like this:

• Splurge Meals (1–2 per trip):
  • Deep dish at one of the classic spots
  • A nice dinner with skyline views or in a buzzy neighbourhood
• Everyday Eats:
  • Hot dogs, Italian beef, and slice joints
  • Grab-and-go lunches near museums or in the Loop
  • Casual brunches in Lincoln Park, Lakeview, or Wicker Park

You’ll save money on the “fuel” meals and feel better about dropping more on those memorable dinners.

Best Time to Visit Chicago (And What to Pack)

Chicago changes dramatically with the seasons. Same city, dramatically different personalities.

Season-by-Season Breakdown

If this is your first time and you’re flexible, aim for late May–June or September–early October. You’ll get warm-ish weather without peak summer chaos.

Sample Chicago Itineraries You Can Actually Use

Let’s take the giant list of things to do and turn it into bite-sized days.

3-Day Chicago Itinerary (First-Time Visitor)

Day 1: Architecture & Downtown Icons

• Morning: Chicago Riverwalk + architecture boat tour
• Midday: Lunch near the Loop, quick wander along the Magnificent Mile
• Afternoon: Millennium Park (Bean, Crown Fountain) + Cloud Gate photos
• Late Afternoon: Art Institute of Chicago
• Evening: Deep dish dinner

Day 2: Museums & Lakefront

• Morning: Field Museum (dinosaurs and SUE)
• Midday: Picnic or quick lunch by the lake
• Afternoon: Shedd Aquarium + lakefront walk to Buckingham Fountain
• Evening: Catch a free concert or movie at the Pavilion in Millennium Park (in season) or a show at Chicago Theatre

Day 3: Neighbourhoods & Views

• Morning: Wicker Park or Lincoln Park wander, café brunch, zoo or park time
• Afternoon: Head up to the Hancock Center or Willis Tower for city views
• Late Afternoon: Lakeside walk or North Avenue Beach
• Evening: Improv at The Second City or a sports game if schedules line up

5-Day Chicago Itinerary (A Bit Deeper)

Add to the 3-day plan:

• Day 4 (Hyde Park & South Side Gems):
  • University of Chicago campus stroll
  • Oriental Institute Museum
  • Osaka Garden
  • Museum of Science and Industry if you’ve got the stamina
• Day 5 (Pick-Your-Own-Adventure):
  • Sports game (Cubs/Bears/Blackhawks)
  • Navy Pier rides + lake cruise
  • Segway or bike tour along the lakefront
  • Money Museum + Magnificent Mile people-watching

Treat this fifth day as your “flex” day to plug in whatever you couldn’t squeeze into the first four.

Chicago on a Budget (Without Feeling Deprived)

Chicago can absolutely chew through your wallet if you let it. But it doesn’t have to.

Free or Nearly Free Things to Load Up On

• Millennium Park (Bean, Crown Fountain, pavilion events)
• Lincoln Park Zoo & Conservatory
• Money Museum
• Lakefront Trail walks and beach time
• Window shopping and people-watching on the Magnificent Mile
• Free or cheap public events in summer: outdoor movies, concerts, festivals

Balance these with a few paid “hero” experiences (architecture cruise, skydeck/observation, one major museum), and your trip will still feel special.

Where to Save vs Where to Spend

Worth Spending On:

• Architecture river cruise
• At least one major museum (Field, Art Institute, or Museum of Science and Industry)
• Observation deck at Willis Tower or Hancock Center
• A proper deep dish meal

Easy Places to Save:

• Buy groceries for breakfast (or simple hotel-room breakfast)
• Use multi-day CTA passes instead of relying on rideshares
• Choose one “big night out” show instead of a packed schedule of expensive evening entertainment
• Pick one or two team sports events, not all three (unless you’re as sports-obsessed as we are)

Practical Tips & Common Mistakes to Avoid

Chicago is generally friendly and easy-going. However, a few little tweaks will make your trip smoother.

Weather & Clothing

• Layers are non-negotiable. Even in summer, evenings by the lake can feel cooler than you’d expect.
• Wind is real. The “Windy City” nickname started for political reasons, but the gusts around the skyscrapers are no joke. A light windproof layer goes a long way.
• Winter isn’t for dabblers. If you’re visiting in January or February, treat it like a proper cold-weather destination: hat, gloves, insulated boots.

Transport & Logistics

• Avoid renting a car unless you’re planning a road trip beyond the city. Parking is expensive, traffic can be stressful, and you genuinely don’t need a car for most city sightseeing.
• When using the ‘L’ late at night, stick to well-lit stations and cars with more people; common-sense city behaviour applies.
• If you’re catching an early flight or train, check how long the transit ride will actually take — those “quick” airport links can still eat up time.

Tickets & Timing

• Popular attractions (architecture cruises, observation decks, some museums) are busiest in the middle of the day and on weekends.
• Whenever you can, book timed-entry tickets in advance and aim for the first slot of the day or late afternoon.
• For sports games and big-name shows, the earlier you buy, the better your odds of decent seats and prices.

Chicago Travel Questions Answered: Practical Tips, Local Advice & Smart Planning for Your Windy City Trip

How many days do I really need in Chicago for a first visit?

Three days. That’s the sweet spot where you’re not rushing like mad but you’re also not stretching the budget too far. With 3 full days you can hit the big architectural sights, at least one major museum, an observation deck, a neighbourhood or two, plus a deep dish feast and an evening show or game. If you only have 2 days, focus on downtown, the river, Millennium Park, one museum, and either Navy Pier or a comedy night. If you’re a museum lover or sports fan, 4–5 days lets you add Hyde Park, more neighbourhoods, and a second game or show without feeling rushed.

What’s the best time of year to visit Chicago for sightseeing and walking?

Honestly, late spring and early fall are gold. Think late May through June or September into early October. You get comfortable daytime temperatures, fewer brutal heatwaves, and way fewer bone-chilling winds than winter. Summer is incredible for festivals, beaches, and outdoor events, but it’s also busy and more expensive. Winter can be magical around the holidays with lights and indoor attractions, but if you’re not used to serious cold, it can be a shock. For a first-timer who wants lots of walking, shoulder seasons win.

Is Chicago safe for tourists around the main attractions and neighbourhoods in this guide?

Mostly yes. The areas you’re likely to focus on as a visitor—The Loop, River North, Magnificent Mile, Lincoln Park, Wicker Park, Hyde Park’s main sights—are busy and generally fine with normal big-city precautions. That means staying aware of your surroundings, not flashing valuables, keeping an eye on your phone and camera, and avoiding lonely side streets late at night. The “L” is widely used, but at night stick to well-lit stations and sit in busier cars. If something feels off, switch cars or grab a rideshare instead. Common sense goes a long way in Chicago.

Do I need to rent a car in Chicago or is public transport enough?

Skip it. Between the CTA ‘L’ trains, buses, Divvy bikes, and walkable central neighbourhoods, you really don’t need a car for a typical tourist trip. Parking is pricey, downtown traffic can be stressful, and many attractions charge for parking on top of admission. Use the Blue Line or Orange Line from the airports, grab a multi-day CTA pass, and mix that with walking and the occasional rideshare at night or after a show. Only consider a rental if you’re tacking on a road trip beyond the city.

Which area is the best place to stay for a first-time visit to Chicago?

If you want easy mode, stay central. The Loop, River North, or the Magnificent Mile put you close to a big chunk of the attractions in this guide. The Loop is ideal for quick access to museums and Millennium Park; it’s quieter at night. River North is better if you want restaurants and nightlife at your doorstep. The Magnificent Mile works if you love shopping and want those skyline-and-river vibes. Lincoln Park is great if you’re okay with a short train ride in exchange for a more local, leafy feel. It really comes down to whether you want to step outside into “classic Chicago” or into a neighbourhood café scene.

How much should I budget per day in Chicago as a mid-range traveler?

Realistically, think in rough bands. On a lean but comfortable budget, you might hover around USD $150–$200 per person per day including lodging (sharing a room), food, transit, and a couple of paid attractions. If you like nicer dinners, cocktails, and multiple paid sights each day, it can easily climb to $250–$300+. You can bring costs down by choosing more free attractions like Lincoln Park Zoo and Millennium Park, buying a transit pass instead of rideshares, and doing quick breakfasts and snacks from grocery stores. Big spends are usually museums, observation decks, architecture cruises, and game tickets.

Is the Chicago architecture river cruise really worth the money compared to just walking the Riverwalk?

Absolutely. Walking the Riverwalk is awesome and free, but the architecture cruise gives you context. Guides unpack the history behind the buildings, the fire, the engineering tricks, and all the little details you’d miss on your own. It’s like switching from just “looking at pretty buildings” to actually understanding why Chicago is such a big deal architecturally. If your budget allows one big “paid” experience, I’d put the river cruise near the top of the list. Then use the Riverwalk for a slower, people-watching stroll later in the trip.

Should I go up Willis Tower or the Hancock Center for city views?

It depends. Willis Tower’s Skydeck and The Ledge are iconic, especially if standing in a glass box over the city is on your bucket list. The Hancock (now 875 N Michigan) has 360-degree views that feel slightly more intimate and also show off Lake Michigan beautifully. Some travelers feel the Hancock is less hectic and more pleasant overall. If you’re nervous about heights, the Hancock often feels a bit less intense while still delivering that “whoa” skyline moment. If you love bragging rights, Willis Tower is the classic choice.

Can I see a Cubs or Blackhawks game without blowing my entire budget?

Yes. You may just need to be flexible. Ticket prices at Wrigley Field and the United Center swing wildly based on the opponent, day of the week, and where you sit. Look at weekday games, upper levels, and seats farther from center ice or home plate to save money. If official tickets look steep, check reputable resale platforms and set alerts. Even a cheap seat is worth it for the atmosphere—singing “Go Cubs Go” at Wrigley or hearing the national anthem at a Blackhawks game is pure Chicago.

Is Chicago a good destination for kids and families?

Definitely. Between Millennium Park fountains, Lincoln Park Zoo, the Shedd Aquarium, the Field Museum, Navy Pier, and beaches like North Avenue, you can easily fill a family itinerary. Most of the attractions in this guide have kid appeal baked in—dinosaurs, jellyfish, Ferris wheels, splash pads, playgrounds. The key is pacing: mix big-ticket indoor attractions with free park time so everyone has space to burn off energy. Stay somewhere with easy transit access and you won’t need to wrangle car seats or downtown parking.

How accessible is Chicago for travelers with limited mobility?

Better than many cities, but still imperfect. Many CTA ‘L’ stations, especially in central areas, now have elevators and are marked as accessible, though not every station is barrier-free yet. Major attractions like the Art Institute, Field Museum, Shedd Aquarium, Navy Pier, and the main observation decks all provide wheelchair access, elevators, and accessible restrooms. Sidewalks downtown are generally good, but winter snow or construction can create obstacles. If accessibility is a priority, pick lodging near accessible ‘L’ stops or planned bus routes and check each attraction’s website for detailed accessibility info before you go.

What’s the best way to get from the airport into the city center?

Simple. From O’Hare, take the Blue Line straight into the Loop; from Midway, it’s the Orange Line. Both run frequently, cost far less than a taxi, and skip traffic jams. If you’re arriving very late, traveling as a big group, or juggling multiple kids and bags, a rideshare or pre-booked shuttle might be worth the extra cost for door-to-door convenience. But for most travelers, the CTA train is the sweet spot between price and practicality.

Is it worth staying near the Magnificent Mile or should I base myself in a neighbourhood like Wicker Park instead?

Both work—it’s about your travel personality. Staying by the Magnificent Mile puts you close to big-name shops, the river, and the lake, which is great for a first trip when you want everything at your doorstep. Wicker Park (and similar neighbourhoods) feels more local: indie cafés, street art, nightlife, and fewer souvenir shops. If it’s your first time and you’re a bit anxious about navigation, go central. If you’re on a second or third visit and want a more “live here for a week” vibe, choose the neighbourhood base and ride the Blue Line downtown when you need your museum and skyline fix.

How brutal is the Chicago winter really, and should I still consider visiting then?

Cold. Properly cold. Wind plus low temperatures can make it feel much harsher than the thermometer suggests, especially by the lake. That said, winter trips have perks: cheaper hotels, fewer crowds at major sights, and a cozy vibe in museums, bars, and cafés. If you’re prepared with a serious coat, hat, gloves, and proper footwear, you can still have a great time focusing on indoor attractions, shows, and sports. If you hate the cold with a passion, though, you’ll enjoy Chicago much more in shoulder season or summer.

What are some easy free or low-cost experiences that still feel “wow”?

Chicago spoils you here. Millennium Park (The Bean, Crown Fountain, pavilion events), Lincoln Park Zoo, the lakefront trail, Buckingham Fountain, the Riverwalk at sunset, free outdoor concerts and movies in summer, and neighbourhood wandering in places like Wicker Park or Hyde Park all deliver big atmosphere for little or no money. Even simply riding the ‘L’ through the Loop for a few stops gives you those elevated-train views that feel straight out of a movie. Stack these freebies next to a couple of paid “hero” activities and your trip still feels rich without your wallet crying.

Chicago Trip Blueprint: Quick Planning Checklist

Here’s a simple checklist you can run through as you plan:

• Decide how many days you realistically have (2, 3–4, or 5+).
• Pick a home base neighbourhood that matches your style (Loop, River North, Lincoln Park, Wicker Park, etc.).
• Choose 2–4 “anchor” experiences: architecture cruise, one observation deck, one or two major museums, maybe a game or show.
• Slot in free/low-cost activities around them: Millennium Park, Lincoln Park Zoo, Money Museum, lakefront walks, neighbourhood wandering.
• Decide on a food game plan: one deep dish meal, one Italian beef/hot dog stop, one splurge dinner, the rest casual.
• Grab a CTA pass or load up a Ventra card for hassle-free transit.
• Pack with the season in mind (layers always, extra cold-weather gear in winter).
• Leave at least one “empty” afternoon or evening for repeat visits to spots you fell in love with.

Chicago is one of those cities that rewards repeat visits. You can hit the highlights on your first trip, then come back for the neighbourhoods, the food, and the sports culture that hook you in for good. And if you’re anything like us, you’ll already be plotting your return before your train or plane even leaves the city.

Final Thoughts From Chicago

And that’s a little preview at our week long visit to Chicago! We tried to cover some of the well-known attractions as well as some sights that lie a little further from the downtown core. We hope this video, photo essay and travel guide will help you plan your next visit to Chicago.

If you’ve already been to the Windy City be sure to leave us a comment and let us know about some of your favorite spots.