The Ultimate Chicago Bucket List

Chicago is an amazing city with hundreds of unique things to do and foods to try. You probably won’t be able to get them all done in a weekend, but you can try and see how many you can check off on your next trip to Chicago! Use this Chicago Bucket list for a unique and exciting Chicago vacation. When you’re done, share your checked off bucket list with me on Twitter or Instagram! 

Chicago Must-Do Bucket List

1. Count the Stars at the Adler Planetarium

The Adler Planetarium, located in Grant Park is also a destination you don’t want to miss! Great date night idea: Adler After Dark.

2. See the Buckingham Fountain Show

Twenty-minute light fountain shows start at dusk. 

3. Meet Sue at the Field Museum

One of the best and largest natural history museums in the world, the Field Museum is a place to meet SUE, the T-Rex!

4. Take an Audio Tour at The Art Institute of Chicago 

The Art Institute of Chicago has the largest collection of Impressionist and Post-Impressionist paintings outside Paris, paintings by Monet, Cézanne, Renoir, van Gogh, and Toulouse-Lautrec. 

5. Go Around the World by Going Around the Tribune Tower

The base of the Tribune Tower has stones from 120 iconic spots around the world in its walls. That way you can lay your hands on the Great Wall of China, Taj Mahal, Parthenon, Alamo, and Notre Dame, in one day.

6. Listen to Jazz at the Chicago Jazz Festival

There are 225 live music venues in all, as well as the Annual Chicago Jazz Festival and the Chicago Blues Festival.

7. See a Show at the Chicago Theatre

Now one of Chicago’s best spots for performing arts, the theatre is owned by the Madison Square Garden Company and puts on a varied program of comedians, world-famous musicians, dance companies, and lectures by renowned cultural figures.

8. Take an Architecture Cruise

Among many other river and lake cruises in Chicago, the Architecture Cruises are known for being the best ones! Go with the Chicago Architecture Foundation River Cruise, and hear fascinating stories behind more than 50 buildings along the Chicago River. It’s a great experience!

9. Visit the Science and Industry Museum

The Science and Industry Museum is the old Palace of Fine Arts, built in 1933 in Jackson Park for the World’s Columbian Exposition. Be sure to visit the Science Storms exhibit, which has a Tesla coil, Foucault pendulum and Wimshurst machine. This is the best science museum I have ever visited!

10. Take a tour of the Sky Chapel at the First United Methodist Church 

Dating back to 1831, the First United Methodist Church of Chicago is the city’s oldest church and tallest church building in the world. The building has 21 floors and reaches 568 feet into the air. Take a free tour of the Sky Chapel at the very top of the building 400 feet above the city Monday through Saturday at 2:00 p.m. or Sunday at 9:45 a.m. or 12:15 p.m.

11. Feel and Breathe the Chicago Culture like a Local

For even more ideas on adventuring Chicago like a local, see 25 Unique Things to Do in Chicago. 

12. Visit the Museum of Contemporary Art

See works by Chuck Close, Andy Warhol, Jasper Johns, Francis Bacon, René Magritte, Alexander Calder, Ann Hamilton and Richard Serra.

13. Stroll down the Riverwalk

Here you will see some of the best views of the city.

14. Visit the Lincoln Park Zoo 

One of the last free zoos in the country.

15. Visit the Bahai Temple

The only Bahá’í house of worship in North America and one of only a handful worldwide. 

16. Find all of the Wizard of Oz Characters at the Oz Park

This whimsical Oz-themed park is a great spot to wander around, and spot the Tin Man, Scarecrow, Cowardly Lion, Dorothy, and Toto. Each character was created by local artist John Kearney.

17. Go Shopping on Magnificent Mile

With 275 restaurants and more than 460 retailers, Michigan Avenue is a whole world of shopping, entertainment, dining, and more things to do than you could manage in a whole holiday. 

18. Ride a bike along the Lakefront Trail

Eighteen miles of Chicago’s shoreline can be accessed on a waterfront path, threading through all four of the city’s lakeside parks. There are bike rental companies all along the trail, or you could buy a day pass for Divvy, Chicago’s bike sharing system.

19. See the Cubs Game

Wear Chicago Cubs attire and see the Chicago Cubs play at the second-oldest ballpark in the Major League. 

20. Go to a Comedy Club

With so many in the city, you have to go to a few, some of the best  ones include the Second City, the Laugh Factory, the Annoyance Theatre, and the iO Theatre. The later the show, the nastier it gets!

Bucket List of Chicago Best Sights

21. See your Reflection in the Cloud Gate (A.K.A. the Bean)

This is where everyone starts their adventure, so should you! Start at the Cloud Gate in the morning (the earlier, the fewer tourists you’ll find) and keep explore Grant Park for a few hours until lunch!

22. Run Under the Crown Fountain

After the bean, keep going to the right if you are looking at the lake, and you will find this unique fountain. This is truly a sight to see, and yes, I dare you to run under the water!

23. Take a Picture at the Ledges of the Willis Tower

The second-tallest building in the Western Hemisphere provides an unrivaled view of a cityscape, from the four glass platforms at 1,353 feet in the air. Located on the Willis Tower’s 103rd floor Skydeck, the observation perches have walls, floors, and ceilings made entirely of glass, “the Ledges”.

24. See the Skyline from the “Chicago Concrete Beach”

Then you can stroll to a sandy Oak Street Beach enjoy the sunshine. 

Summer Chicago Bucket List

There is even more to do in Chicago in the summer!

25. Have a Picnic in the Lincoln Park 

Nice and relaxing afternoon with beautiful views of the skyline – a must for a summer day. 

26. Go to the Beach and Swim in Lake Michigan 

Who knew Chicago has amazing beaches? You didn’t? Take on the challenge at North Avenue Beach, Montrose, or Foster. No wonder they call Chicago the third coast.  

27. Attend One of Many Chicago Festivals

There is something going on every weekend. In March you can see the Green River on St. Patrick’s Day, and in the summer you should attend the Duck Race, the Rib Festival and the famous Airshow in Chicago. 

28. Take a Lake Booze Cruise 

I recommend using one of the Groupon deals for this one. 

29. Go Kayaking Down the Chicago River

One of the most fun and unique ways to experience the city.

30. See the Summer Fireworks

All summer long on Wednesday and Saturdays, go downtown to see the fireworks (or almost anywhere south of Montrose Beach along the lakeside trail). 

31. Go to the Navy Pier

If you like to shop in the middle of the lake, head over to the Navy Pier. 

Foodie Chicago Bucket List

Chicago is foodie heaven. You are literally in heaven. 

32. Have a Deep Dish Pizza

Try them all, start with Giordanos, then move on to Bacino’s of Lincoln Park, then to Pequod’s and finish at Lou Malnati’s. Now, tell me your favorite in the comments below! 

33. Go on a World Foodie Tour Without Leaving Chicago

Taste the world in Chinatown, Greektown, Pilsen, Little India, and the Ukrainian Village.

34. Try a Chicago-style Hotdog

It’s even better at a street stand.

35. Try Real Chicago-style Popcorn

Have you heard of Chicago-style popcorn? Head to Garret’s Popcorn Stores (all over the city) and order a fan-favorite cheese and caramel mix. 

36. Get Drinks at the Signature Lounge

Instead of paying for the 360 experience, get a drink at the Signature Lounge one floor above at the John Hancock Center. One of my favorite views of Chicago.

37. Print and use the Chicago Bucket List below to check off  all of the destinations you visit! When you’re done, share it with me on Instagram!

Did I miss anything? See my bucket list progress on my Instagram Page Highlights and let me know what’s on your Chicago Bucket List in the comments below!