35 Things to do in Chicago

35 Things to do in Chicago Travel Guide

35 things to do in Chicago travel guide
35 things to do in Chicago travel guide

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:

Chicago Travel Video

Chicago Photo Essay

Downtown Chicago architecture
Downtown Chicago architecture

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.

Downtown Chicago boat trip architecture tour down the Chicago River
Downtown Chicago boat trip architecture tour down the Chicago River

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.

Kayaking down the Chicago River
Kayaking down 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.

Reflection and photography from the Cloud Gate also known as the Bean
Reflection and photography from the Cloud Gate also known as the Bean

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.

Children playing and splashing at Millennium Park in downtown Chicago
Children playing and splashing at Millennium Park in downtown Chicago

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.

Watching a free movie outside at the Pavilion nearby Millennium Park
Watching a free movie outside at the Pavilion nearby Millennium Park

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!

Lion statue just outside of the Art Institute of Chicago
Lion statue just outside of the Art Institute of Chicago

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.

I'm a die hard Chicago Cubs baseball fan. Pity me!
I’m a die hard Chicago Cubs baseball fan. Pity me!

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.

Audrey Bergner of That Backpacker posing with Chicago Deep Dish Pizza from Lou Malnati's
Audrey Bergner of That Backpacker posing with Chicago Deep Dish Pizza from Lou Malnati’s

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 😉

Daytime views from the Willis Tower formerly known as Sears Tower
Daytime views from the Willis Tower formerly known as Sears Tower

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.

Ivy on a building located on campus at the University of Chicago
Ivy on a building located on campus at the University of Chicago

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.

The Oriental Institute Museum at the University of Chicago
The Oriental Institute Museum at the University of Chicago

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.

Scenic views from the Osaka Garden located on Chicago's South Side of the city
Scenic views from the Osaka Garden located on Chicago’s South Side of the city

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.

Graffiti at Wicker Park in Chicago
Graffiti at Wicker Park in Chicago

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.

Scenic views from Humboldt Park in Chicago
Scenic views from Humboldt Park in Chicago

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.

T-Rex 'Sue' at the Field Museum in Chicago
T-Rex ‘Sue’ at the Field Museum in Chicago

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?

Jellies at the Shedd Aquarium in Chicago
Jellies at the Shedd Aquarium in Chicago

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.

Bobby Hull Statue at the United Center home of the Chicago Blackhawks

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.

Audrey Bergner That Backpacker striking poses at the Borders exhibit in Solti Park
Audrey Bergner That Backpacker striking poses at the Borders exhibit in Solti Park

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 😉

Buckingham Fountain at night in Chicago
Buckingham Fountain at night in Chicago

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.

Chicago skyline at night from the Hancock Center
Chicago skyline at night from the Hancock Center

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.

Navy Pier Park in Chicago
Navy Pier Park in Chicago

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.

A Lion stretching out to sleep at Lincoln Park Zoo
A Lion stretching out to sleep at Lincoln Park Zoo

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.

Ladies wearing bikinis at North Avenue Beach in Chicago
Ladies wearing bikinis at North Avenue Beach in Chicago

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.

Second City Comedy Club in Chicago
Second City Comedy Club in Chicago

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.

Trapped in a Room with a Zombie
Trapped in a Room with a Zombie

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 😉

Sitting down on a Chicago Blackhawks chair along the Magnificent Mile
Sitting down on a Chicago Blackhawks chair along the Magnificent Mile

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.

The Chicago L from above in the downtown area
The Chicago L from above in the downtown area

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.

Chicago Bears fans strolling along Navy Pier
Chicago Bears fans strolling along Navy Pier

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.

Audrey Berger That Backpacker as an American two dollar bill
Audrey Berger That Backpacker as an American two dollar bill

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!

Riding a bicycle in Chicago as a small child drinks Pepsi
Riding a bicycle in Chicago as a small child drinks Pepsi

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 😉

The Museum or Science and Technology in Chicago
The Museum or Science and Technology in Chicago

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.

A close up shot of Robbie House in the south side of Chicago
A close up shot of Robbie House in the south side of Chicago

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.

Zipping around the downtown area of Chicago by Segway
Zipping around the downtown area of Chicago by Segway

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.

The iconic Chicago Theater by day
The iconic Chicago Theater by day

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.

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.

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  12. says: Michael freeman

    You guys left out the night life like crowbar night club and rush and division. Just moved to Austin TX but lived in chi town for 18 yrs. I love chicago

  13. says: Fly Girl

    Hey Samuel,
    I have to commend you for doing such a balanced job of covering the great experiences in my city. People don’t typically venture past the North Side so i really appreciate that you included U of C, Humboldt Park and Osaka Gardens, where I actually got married. I’d also add the Chicago Cultural Center, which boasts the world’s largest Tiffany Dome as well as fee concerts, movies and exhibits. A small correction is the Museum of Science and Industry, not Technology and I really believe you meant to list the winning White Sox and not the losing Cubs but I forgive you!

  14. says: todd

    Many years ago I went up to the top floor of the Willis Tower (called the Sears Tower back then) and the view is breathtaking. I was up there for four hours just enjoying the view. Next time I need to check out the view from the Hancock tower.

  15. says: Cristy

    Chicago is definitely one of the loveliest cities in the world. It is the filming location of one of the Bollywood movies that I watched. I want to go the Bean one day!!! 🙂

  16. says: Alex

    Lou Malnati’s is the best, hands down! As a native Chicagoan, my favorite part of the city is the food scene. Longman and Eagle, Bite Cafe, Naha, Schwa, Kuma’s Corner, Hot Dougs, Big Star, Crisp, Little Goat, etc.

  17. says: The Guy

    You timed your visit to Willis Tower perfectly, I love that picture with the foggy city.

    I’ve never made it to Chicago (apart from O’Hare) so will have to visit at some point. This is a fabulous checklist and am sure would keep me very busy.

    As for supporting a sporting team with very limited success in recent times, I know all about that!

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  19. says: Kendra (the Escapologist)

    I can’t believe I’ve never been to Chicago! It’s such an easy flight from NYC. I must visit before I leave on my RTW trip! Humboldt park looks beautiful.

  20. We’ve never been to Chicago and this is extremely inspiring to go! Phenomenal job with this guide- amazing photos and wonderfully diverse. You have something for everyone covered!

    As we’re now living in Boston we’ll definitely be getting to Chicago at some point soon and we’ll certainly re-visit this post again when we do. Again, AWESOME job!! 😀

  21. says: Anna @ It Started in Asia

    What an awesome wrap up! The fog over the city skyline has certainly made for some magical pics 🙂

  22. says: tracy

    Great information and photos. My favorite thing about Chicago are actually the fabulous restaurants. One of my favorites is RPM Italian.

  23. says: Gina

    Love Chicago! This is such a great, comprehensive list. I’m pretty sure it doesn’t get much better than #9 though – loooove the pizza, especially at Giordano’s. 🙂

  24. says: Sofie

    Loving the side wide post!
    Makes both the photos and video come out great.
    Chicago is definitely on my list of cities I want to visit, but preferably in summer as well:D

    1. Thanks Rhonda! We had a wonderful 3 week trip including our time in Montreal and New York City. It has made me realize how much I want to travel more in Canada and the US after having spent so much time abroad. Lou Malnati’s is awesome!

  25. says: Renuka

    That’s a wonderful list! I must admit I never expected Chicago to be so exciting. As a traveler, I am mostly inclined toward European countries and cities, but Chicago is FULL OF LIFE.

  26. Eating a deep dish pizza and going to see a Cubs game are hands down the 2 best things to do in Chicago. If you ever head out to the suburbs a little bit, there’s a hot dog place called “Gene and Judes” which sell Chicago style Vienna hot dogs. If you ever get a chance, try that place out! Trust me, the long line is worth it! I love Chicago!!

    1. Thanks Hannah! What a great suggestion. I also had someone recommend Hot Doug’s as well. That is one thing we totally missed out on doing! Another reason for us to go back I suppose 🙂

  27. says: Maria Falvey

    I always enjoy your “what to do” posts Sam – you show the popular highlights as well as spots others might overlook. This post on Chicago is no different and I thank you for that. Kudos!

    1. Thanks Maria! That is definitely always our goal: to highlight the top attractions but also to cover places that might otherwise be overlooked. It is too bad we didn’t have a couple more days in the city because I wanted to cover more of the neighborhoods.

  28. says: Sarah

    Wow these photos make me feel as if I am there. I LOVED the architecture tour given aboard the city river tour. The guides gave so many tidbits and snippets of funny stories. I never looked at the city the same way again. Did you have a favorite story about the city? Or a personal story from Chicago?

  29. says: Charlie

    Damn. When I was living in Canada I kept meaning to go visit Chicago (as I was so much closer to it than here in the UK) and never got round to it. Totally regretting it now, it seems like a great city! I was writing about Chicago Tilt at the 360 Chicago for work the other day, seems like a pretty cool experience, adds a bit more excitement to an observation tower. I love the foggy skyline, photo by the way!

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  35. says: Candice @ The Let's Go Ladies

    Oh man, I need to go to Chicago STAT. I was going to mention one or two places that you wrote about as “must-see” for me, but I lost count after 10 or so! Definitely putting Chicago high up there on my travel bucket list. Thanks for such an awesome post, bookmarking it right now.

    1. I know what you mean Buddy! Being abroad for such a long time has allowed me to come back home to North America with fresh eyes. I want to do an epic road trip across Canada/USA!