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

Glorious History Of Chicago For Visitors

Ah, the Windy City – home of the hot dog, deep dish pizza, and a whole lot of history. Founded in 1833, Chicago has been around for over 180 years and boy, has it seen some things.

Once upon a time, Chicago was just a small town on Lake Michigan, but then came the railroad and boom – instant growth! Who needs natural resources when you can transport goods and people across the country?

Chicago’s involvement in the Civil War was also pretty significant. Many of its residents served in the Union Army and let’s not forget those famous Lincoln-Douglas debates that really helped to solidify… something or other. I’m sure it was important.

But what really put Chicago on the map was the Great Chicago Fire of 1871. The city was burned to the ground, but did they give up? No way! They rebuilt and made some iconic buildings and structures, like the Willis Tower and the Chicago Water Tower. Who needs fire safety regulations anyway?

In the 20th century, Chicago became a center of culture and entertainment, with institutions like the Art Institute of Chicago and the Chicago Symphony Orchestra. And of course, let’s not forget the city’s most famous residents: Walt Disney, Oprah Winfrey, and Barack Obama. Who needs Hollywood when you’ve got the Windy City?

Today, visitors to Chicago can experience the city’s rich history through a variety of attractions and landmarks, such as the Chicago History Museum and the Willis Tower Skydeck. Just be sure to hold onto your hats because that wind can be pretty brutal.

In all seriousness, Chicago is a city with a fascinating history and is definitely worth exploring. But hey, a little sarcasm and humor never hurt anyone.

Chicago Photo Essay + Things To Do In The Windy City

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.

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.

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.

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.

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.

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!

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.

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.

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 😉

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.

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.

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.

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.

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.

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.

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?

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.

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.

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 😉

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.

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.

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.

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.

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.

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.

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 😉

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.

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.

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.

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!

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 😉

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.

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.

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.

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.

Chicago Accommodations: Range For All Budgets

Alright, listen up folks! If you’re planning a trip to Chicago, you better be ready to choose from a wide range of accommodations to suit your every need and desire. No matter what kind of traveler you are, Chicago has got you covered.

For those looking to ball out, Chicago’s got some serious luxury options. The Four Seasons Hotel Chicago and The Langham, Chicago are the cream of the crop, offering unparalleled service, amazing views, and all the fancy amenities you could possibly want.

Mid-range travelers don’t have to sacrifice style and comfort either. Hotels like The James Chicago and The Gwen offer chic and convenient accommodations in the heart of the city without breaking the bank.

But hey, if you’re trying to save some cash, don’t worry – Chicago’s got plenty of budget-friendly options too. Hostels like HI Chicago and Freehand Chicago offer affordable dorms and private rooms, as well as social events and activities for guests.

And of course, let’s not forget about Airbnb. With thousands of listings throughout the city, you’re sure to find the perfect spot to call home during your visit to the Windy City. From cozy apartments to spacious lofts, there’s something for everyone on the platform.

So whether you’re looking to live like a king, ball on a budget, or anything in between, Chicago’s got you covered. So pack your bags, choose your spot, and get ready for an unforgettable stay in one of America’s greatest cities.

Chicago Day Trips

Are you tired of the hustle and bustle of Chicago? Want to get out of the city and explore some amazing destinations nearby? Well, buckle up and get ready for an adventure because I’ve got some incredible day trips for you to check out!

First up, we’ve got Milwaukee, Wisconsin – a city bursting with culture and creativity. From world-renowned breweries to fascinating museums and galleries, there’s something for everyone in Milwaukee. And let’s not forget about the delicious cuisine! You won’t find better cheese and beer anywhere else.

Next on the list is Starved Rock State Park – a natural wonderland just a short drive from Chicago. With stunning waterfalls, breathtaking canyons, and plenty of hiking trails, this park is a nature lover’s dream come true. Get ready to take in some fresh air, get some exercise, and marvel at the beauty of the great outdoors.

If you’re looking for a beachy escape, head on over to Indiana Dunes National Park. This hidden gem boasts incredible views of Lake Michigan, white sandy beaches, and some seriously impressive sand dunes. Plus, it’s just a quick drive from the city – making it the perfect destination for a day trip.

For history buffs and architecture enthusiasts, Galena, Illinois is the place to be. This charming town is full of historic architecture, unique shops, and incredible restaurants serving up some seriously delicious food. You won’t want to leave this picturesque town – trust me!

Last but not least, Michigan City, Indiana is a must-visit destination for anyone looking to escape the city and get back in touch with nature. With stunning beaches, rolling sand dunes, and plenty of local shops and restaurants, this town is the perfect spot for a relaxing day trip.

So what are you waiting for? Get out there and explore all the amazing destinations that the Windy City has to offer. Whether you’re a foodie, a nature lover, or just looking for a change of scenery, these day trips are sure to satisfy your wanderlust.

Chicago Summer Festivals

Chicago is known for its vibrant summer festival scene, with events taking place throughout the city from May through September. Here are some of the best summer festivals in Chicago:

1. Chicago Blues Festival: The Chicago Blues Festival is the largest free blues festival in the world, taking place in Millennium Park in June. The festival features performances by local and national blues musicians.
2. Taste of Chicago: The Taste of Chicago is a food festival that takes place in Grant Park in July. The festival features food from more than 80 Chicago restaurants, as well as live music and other entertainment.
3. Lollapalooza: Lollapalooza is a four-day music festival that takes place in Grant Park in August. The festival features performances by some of the biggest names in music, as well as up-and-coming artists.
4. Chicago Jazz Festival: The Chicago Jazz Festival is a free music festival that takes place in Millennium Park in August. The festival features performances by local and national jazz musicians.
5. Chicago SummerDance: Chicago SummerDance is a series of free outdoor dance events that takes place in Grant Park from June through September. The events feature live music and dance lessons in a variety of styles, from salsa to swing.
6. Chicago Air and Water Show: The Chicago Air and Water Show is a free event that takes place on the lakefront in August. The show features aerial demonstrations by military and civilian aircraft, as well as water-based stunts by the U.S. Navy Blue Angels and U.S. Army Parachute Team.

These festivals are just a few of the many events that take place in Chicago during the summer months. Attending one or more of these events can be a great way to experience the city’s culture, music, and food while enjoying the summer weather.

Chicago Summer Tours

Chicago offers a variety of tours during the summer months that allow visitors to explore the city’s history, culture, and landmarks. Here are some popular summer tours in Chicago:

1. Architecture boat tour: A popular way to explore Chicago’s famous architecture is by taking an architecture boat tour on the Chicago River. These tours offer stunning views of the city’s skyscrapers and allow visitors to learn about the history and design of some of Chicago’s most famous buildings.
2. Bike tour: Another fun way to explore the city is by taking a bike tour. There are many bike tour companies in Chicago that offer guided tours of various neighborhoods and attractions, including the lakefront, Lincoln Park, and the famous murals of Pilsen.
3. Food tour: Chicago is known for its food, and a food tour is a great way to experience some of the city’s best eats. There are many food tour companies in Chicago that offer guided tours of various neighborhoods, including Little Italy, Greektown, and Pilsen.
4. Segway tour: For a unique and fun way to explore the city, consider taking a Segway tour. These tours offer a guided experience on a Segway, allowing visitors to cover more ground and see more sights than they might be able to on foot.
5. Trolley tour: Another popular way to explore the city is by taking a trolley tour. These tours offer a guided experience on a trolley, allowing visitors to see some of Chicago’s most famous landmarks and neighborhoods, including the Loop, Navy Pier, and Wrigleyville.

By taking one or more of these tours, visitors can gain a deeper understanding of Chicago’s culture, history, and landmarks while enjoying the beautiful summer weather.

Chicago Transportation Guide

Chicago offers a variety of transportation options for visitors during the summer months. Here is a guide to help you navigate the city’s transportation:

1. Public transportation: Chicago has an extensive public transportation system that includes buses and trains operated by the Chicago Transit Authority (CTA). The CTA is a convenient and affordable way to get around the city, with routes that serve downtown and many of the city’s neighborhoods.
2. Divvy bikes: Divvy is a bike-sharing program that operates throughout the city, with bike stations located throughout downtown and many neighborhoods. Visitors can rent bikes for a single ride or purchase a day pass or multi-day pass for unlimited 30-minute rides.
3. Ride-sharing services: Services like Uber and Lyft are also available in Chicago and can be a convenient way to get around the city. Visitors can use these apps to request a ride and be picked up at their location.
4. Taxis: Taxis are readily available throughout the city, and visitors can hail them on the street or use ride-hailing apps like Curb to request a ride.
5. Walking: Many of Chicago’s neighborhoods are pedestrian-friendly and can be explored on foot. Walking is a great way to see the city’s architecture, parks, and public art installations.
6. Water taxis: Water taxis are a unique way to travel along the Chicago River and Lake Michigan. Several water taxi services operate in the city, with stops at various locations, including Navy Pier and the Willis Tower.
7. Sightseeing buses: Sightseeing buses are a popular way to explore the city’s landmarks and attractions. These buses offer hop-on, hop-off tours with narrated commentary, allowing visitors to see the city at their own pace.

By using these transportation options, visitors can easily get around the city and explore all that Chicago has to offer during the summer months.

Chicago Foods To Try In The Summer

Chicago is known for its food, and in the summer, there are some dishes and drinks that are especially popular. Here are some Chicago foods to try during the summer:

1. Chicago-style hot dog: A Chicago-style hot dog is an all-beef hot dog served on a poppy seed bun and topped with yellow mustard, bright green relish, chopped onions, a dill pickle spear, tomato slices, sport peppers, and a sprinkle of celery salt. You can find these at many hot dog stands throughout the city.
2. Italian beef sandwich: Another iconic Chicago dish is the Italian beef sandwich. Thinly sliced beef is cooked in spices and served on an Italian roll with sweet or hot peppers and a spicy au jus dipping sauce. Try one at Al’s Beef or Portillo’s.
3. Deep-dish pizza: Chicago is famous for its deep-dish pizza, which has a thick, buttery crust and is loaded with cheese and toppings. Some popular places to try deep-dish pizza are Lou Malnati’s, Giordano’s, and Gino’s East.
4. Rainbow cone: Rainbow cone is a Chicago classic dessert that consists of several layers of different flavors of ice cream, including chocolate, strawberry, Palmer House (vanilla with cherries and walnuts), pistachio, and orange sherbet. You can find it at the original Rainbow Cone stand on the South Side.
5. Craft beer: Chicago has a thriving craft beer scene, and in the summer, many breweries and beer gardens open their doors to visitors. Some popular breweries to check out include Revolution Brewing, Half Acre Beer Company, and Goose Island Brewery.
6. Margarita: Chicago’s hot summer weather calls for a refreshing drink, and a margarita is a great choice. Try one at Big Star in Wicker Park or at one of the many rooftop bars throughout the city.
7. Garret Popcorn: Garret Popcorn is a Chicago institution, known for its famous “Chicago Mix” popcorn, which combines caramel corn and cheese corn. Grab a bag at one of their many locations throughout the city.
8. Tacos al pastor: Tacos al pastor, a Mexican dish made with marinated pork cooked on a vertical spit, are a favorite in Chicago. Head to one of the city’s many taquerias, like La Pasadita or L’Patron, to try them.
9. Chicago-style Italian ice: Italian ice is a refreshing treat on a hot day, and in Chicago, you can try it in the city’s signature style, with a layer of soft-serve ice cream at the bottom. Get one at Johnnie’s Beef or Mario’s Italian Lemonade.
10. Chicago-style popcorn: In addition to Garret Popcorn, Chicago is also known for its unique style of popcorn, which is coated in a sweet and buttery caramel sauce. Try some at Nuts on Clark or Popcorn Palace.

By trying these Chicago foods and drinks, you can experience the city’s culinary scene and get a taste of what makes it so unique.

Chicago On A Shoestring Budget

Chicago can be a great destination for budget travelers during the summer months. Here are some tips to help you experience the city without breaking the bank:

1. Free attractions: Chicago is home to many free attractions, including Millennium Park, Navy Pier, Lincoln Park Zoo, and the Chicago Cultural Center. Take advantage of these attractions to enjoy the city without spending a dime.
2. Public transportation: The Chicago Transit Authority (CTA) offers affordable and convenient transportation options throughout the city. Purchase a Ventra Card or use your contactless payment card to pay for fares on buses and trains. Consider getting a multi-day pass to save money on transportation costs.
3. Street food: Chicago is known for its delicious street food, from hot dogs to deep-dish pizza. Eating at food trucks and food stalls can be a cheaper alternative to sit-down restaurants.
4. Explore neighborhoods: Chicago is a city of neighborhoods, each with its own unique character. Take a walk or bike ride through neighborhoods like Wicker Park, Logan Square, and Pilsen to experience the local culture.
5. Free events: During the summer, there are many free events and festivals in Chicago. Check out the city’s events calendar to find out what’s happening during your visit.
6. Hostels and budget hotels: Chicago has many hostels and budget hotels that offer affordable accommodations. Consider staying in neighborhoods like Wrigleyville, Lincoln Park, or Lakeview to save on lodging costs.
7. Free walking tours: Many organizations offer free walking tours of Chicago, including the Chicago Greeter program, which pairs visitors with local volunteers who show them around the city.

By following these tips, you can experience the best of Chicago while keeping to a shoestring budget.

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.

Chicago, oh Chicago, the Windy City fair, A city of skyscrapers that rise into the air. From Lake Michigan’s shore to the downtown street, There’s so much to explore, so much to eat.

In summer, the city comes alive, The vibe is electric, it’s hard to describe. From Navy Pier’s fireworks to Grant Park’s festivals, There’s always something that’s sure to dazzle us.

Take a stroll down the Magnificent Mile, Or catch a game at Wrigley Field with a smile. Soak up the sun at North Avenue Beach, Or dance to the beats at Lollapalooza, just out of reach.

Indulge in deep-dish pizza, hot dogs, and more, Chicago’s food scene is one to adore. From Michelin-starred restaurants to street vendors’ fare, The taste of the city will leave you wanting to share.

But it’s not just the food and the sights that are grand, It’s the people, the culture, that make Chicago stand. From blues clubs to improv, the arts are alive, Chicago’s summer scene is one you’ll never survive.

So come to Chicago, the Windy City bright, Where summer’s a dream, and the days are just right. A city that’s bold, a city that’s true, Chicago’s the place to be, for me and for you.

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.