This Chicago bucket list got a little longer than I expected.

Fun Free and Cheap Things to Do in Chicago

There are a lot of fun, inexpensive things to do in the Windy City! And unlike some American cities, there’s plenty of public transportation (the El, for instance), which also helps with the budget. I think it’s very cool that some of Chicago’s top tourist attractions are free. In fact, you could put together an amazing visit and never pay a price for admission

1. Take in the Chicago Riverwalk.

Outdoor restaurants and rooftop bars line this thoroughfare, and there’s public art, too—including the fabulous Art on the Mart giant-scale video installations at 9 and 9:30 pm.

2. Visit Millennium Park and the Bean.

If you don’t get a photo at the Bean, have you really been to Chicago? Sir Anish Kapoor, the British artist who created it, named this amazing work Cloud Gate. I read once that he hated the “Bean” nickname at first but warmed up to it. Walk right under the Bean and look up. It may take you a minute to spot yourself in the fractal-like reflections of seemingly infinite depth.

While you’re at Millennium Park, don’t miss Crown Fountain. You can get a cheap meal from a food truck and enjoy the video installation.

3. Visit Buckingham Fountain.

Another classic photo op! This is right by Lake Michigan and an easy walk from the Bean and the Chicago Art Institute. Every time I go, I forget how big it is.

4. Go to the Lincoln Park Zoo.

This is a beautiful zoo, and it blows my mind that it’s free.

5. Meander in the Lincoln Park Observatory.

Take time to stop and smell the orchids—they’re amazing. One of them smells like chocolate mint.

6. Take in the beauty of the Garfield Park Observatory.

7. Connect with nature at the Chicago Botanic Garden.

Another lovely place!

8. Spend some time in the Harold Washington Library Center.

If you’ve known me for five minutes, you knew a library would be on the list. This one is named after a former Chicago mayor, and it’s a beautiful place.

9. Contemplate art at the Smart Museum of Art at the University of Chicago.

10. Get inspired at the National Museum of Mexican Art.

This is in the Pilsen neighborhood, where one of my nieces lives now. It’s a great little museum and I want to go back soon!

11. Visit the Chicago Cultural Center.

12. Encounter creative visions at the Museum of Contemporary Photography.

13. Get a picture with the Picasso statue.

This gigantic horse thing on Daley Plaza is really striking.

14. Get your picture with Calder’s Flamingo.

Another famous sculpture. This one is at 50 W Adams Street, and it’s bright orange and huge—you can’t miss it!

15. Attend a free summer music concert or festival.

There are a lot of choices in the summer!

16. Take a walk in the Pullman Historic District.

17. Take a walk on the 606 Trail.

18. Take a walk on the Michigan Avenue Bridge.

A tourist favorite with lots of great photo opportunities.

19. Get your photo by the “Greetings from Chicago” mural in Logan Square.

20. Take a Free Tour by Foot.

Here’s the link!

Iconic Things to Do in Chicago

These are some of the top tourist attractions in Chicago, in my opinion…although I already listed a few of those above, like the Bean!

21. Go to the Chicago Art Institute.

This is a stately, world-class museum that takes numerous visits to truly appreciate. You can see Ed Hopper’s Nighthawks, Georges Seurat’s A Sunday on la Grande Jatte, Picasso’s Blue Period painting The Old Guitarist…I could go on and on, but my two favorite pieces are the big Georgia O’Keefe over the stairwell and Chagall’s breathtaking America Windows. By the way, if you live in Illinois, the museum is free on Thursdays!

22. Stroll and shop on the Magnificent Mile.

This is a good one to combine with the Art Institute, above. The Magnificent Mile, a stretch of Michigan Avenue bordered by Oak Street and the Chicago River, is one of the most attractive city boulevards in America. Besides high-end shops, you’ll encounter landmarks like the old Chicago Water Tower, the Tribune Tower, the Wrigley Building, and the John Hancock skyscraper.

23. Ride the huge Ferris wheel at Navy Pier.

You’ll need advance tickets for this. The whole Navy Pier area is a favorite tourist attraction and fun to visit whether you go up in the big wheel or not.

24. See a Cubs game.

Go, Cubs, go!

25. See a White Sox game.

26. Step out into the air at Willis Tower.

I wanted to write “Sears Tower,” but the name officially changed to Willis Tower years ago. Many Chicagoans have never fully accepted that. It’s 108 stories tall, and as someone who has no fear of heights, I loved stepping out onto the glass skydeck here a few years back, but you may prefer to enjoy the view with the solid, opaque floor beneath you.

27. Meet ocean life at the Shedd Aquarium.

With seven different exhibit sites, the Shedd may take several visits to see in its entirety.

28. Go to a blues bar!

Chicago is famous for the blues (though Memphis lays claim to it, too.) You can try Rosa’s, Kingston Mines, or many other places.

29. Marvel at Earth’s history at the Field Museum.

This museum of natural history is famous for Sue, its giant T. Rex fossil, and they’ve done a great job with the presentation about her. Check out the hall filled with priceless jewels, too.

30. Expand your thinking at the Museum of Science and Industry.

This is a favorite for children and school groups, but it’s just as much fun (and still enlightening!) for adults.

More of the Best Museums in Chicago

Chicagoland has some of the best museums in the United States. Here are some more to check out!

31. Go to the American Writers Museum.

We’re going this weekend!

32. Go to the Museum of Contemporary Art.

33. Go to the Richard H. Driehaus Museum.

Photo from their website. This whole place looks gorgeous.

34. Learn fascinating history at the Chicago History Museum.

This is next to Lincoln Park Conservatory and Zoo in Lincoln Park, so you could make a day of it.

35. Check out Chicago’s famous Water Tower Museum.

36. Learn about European immigrant history at the Swedish American Museum.

I really enjoyed this place! It’s in the Andersonville neighborhood.

37. Admire ancient artifacts at the Oriental Institute Museum.

38. Learn about African-American history at the DuSable Museum.

I’ve been here! It’s a fantastic museum.

39. Visit the Pritzker Military Museum & Library.

40. Check out the Ernest Hemingway Birthplace Museum in Oak Park.

Fun Things to Do For Your Birthday in Chicago

Admittedly, anything on this list would qualify, but I think these are particularly good for commemorating birthdays and special occasions.

41. See feats of valor at Medieval Times.

There’s a Schaumburg, IL location, and for a few reasons, I have a deep fondness for it. I think it’s funny that I wound up living pretty much right by it. I went there years ago for a milestone birthday, and I went again recently to kick off our staycation! They’ll announce your birthday during the feast.

By the way, if you’re not sure what Medieval Times is all about, this SNL skit depicts it pretty accurately, except there are gorgeous horses doing amazing tricks at the real Medieval Times, and there’s no off-script Adam Driver.

42. Enjoy a Chicago Lunch Cruise on Lake Michigan.

Like this one!

43. Go on a Chicago River Floating Tiki Boat Tour.

Here’s the link! It’s hard to get more festive than floating on a party boat in the city.

44. Celebrate at RAISED, a rooftop bar in the river district area.

45. Have brunch on the rooftop patio at Etta in Bucktown.

46. Find your serenity at AIRE ancient baths.

I can’t wait to check out this unique spa in a converted factory in River West, where they’ve recreated the ancient Roman, Greek, and Ottoman bath experience.

47. Meditate at the Chicago Zen Buddhist Temple.

Clear your head for another trip around the sun.

48. Play air hockey and classic arcade games at FTW Chicago.

I want to take my nephew and nieces to this arcade for adults. There’s also a mini golf course inside.

49. Take a fishing charter trip on Lake Michigan.

50. Go to Six Flags Great America.

This amusement park isn’t far from Chicago, in Gurnee, IL.

Parks and Nature Preserves in the Chicago Area

Chicago’s a big city, but you’re never far from nature. Going to a botanical garden or a nature preserve is one of my favorite ways to spend a Saturday, and some of these can also be filed under “free things to do in Chicago.”

51. Visit Jackson Park’s Japanese Garden.

52. Visit Lurie Garden.

53. Check out the Gethsemane Garden Center.

54. Spend an afternoon at the Morton Arboretum.

I love this place, and it’s really big. The last time I was there, they had a wonderful large-scale sculpture exhibit.

55. Visit Columbia College Garden.

56. Take a stroll in Grant Park.

57. Explore the Klehm Arboretum & Botanical Garden.

58. Take a road trip to Indiana Dunes National Park.

It’s a short road trip and a great getaway. As someone who moved from LA to Chicago, I’ve really been struck by how much Lake Michigan feels like the ocean.

59. See some bison at the Midewin National Tallgrass Prairie.

Depending on the season, you may see a lot of monarch butterflies, too! This is also a short road trip. When I wrote a poem about this place, I had no idea I’d ever live close to it. A very long time ago, there was a native American community on this site, and not so long ago, it was an ammunition plant. I love it that it got turned back into a prairie.

60. Explore a nature trail at Kankakee River State Park.

This isn’t too far from Midewin, and I bet it’s gorgeous in the fall.

61. Go to the Oak Park Conservatory.

They have a talkative and sassy parrot. This is in walking distance of Kettlestrings Tavern, which is a nice brunch or lunch spot.

62. Enjoy Lake Shore East Park.

63. Take a walk at Buffalo Creek Nature Preserve.

This is in the northwest suburbs. Let me tell you, the deer here are not afraid of people.

64. Talk a walk in the sculpture park in Schaumburg.

Also in the northwest suburbs. I believe the official name is The Chicago Athenaeum’s International Sculpture Park.

65. Check out the North Park Village Nature Center.

An oasis of nature, right in the middle of the city.

Great Architecture in Chicago

Not everybody knows this, but Chicago is the birthplace of the skyscraper, and it’s home to some of the most beautiful, award-winning architecture in the United States. Here are some architectural tourist attractions!

66. Take a river and lake architecture tour.

I absolutely loved this tour, and most people will tell you the same. It’s a great way to see the city and learn so much about the stories behind the beautiful buildings, old and new. My two favorite buildings, Aqua Tower and St. Regis Chicago, are both stunning newer additions to the skyline; Jeanne Gang and her studio designed them both.

Architecture appreciation aside, it’s fun to be out on the water, and even as someone who’s prone to motion sickness, I didn’t get queasy.

67. Visit the Frank Lloyd Wright Home and Studio.

Learn more about one of the greatest American architects.

68. Visit Frank Lloyd Wright’s Robie House.

69. Take stunning photos at the Rookery Building.

70. Go up to the observation deck at the John Hancock Center.

Some people say this has better views than Willis Tower, but I still need to check it out.

71. Take a Chicago walking tour of Art Deco skyscrapers.

Here’s the link!

72. Take a Workers Cottages of Oldtown Triangle Walking Tour.

And here’s the link for that one!

73. Check out the Wrigley Building.

74. Stop by the Old St. Patrick Church.

75. And you’re definitely going to want a photo of Marina City.

Eating Famous Foods in Chicago

76. Get a classic Chicago-style hot dog.

Portillo’s is a good bet for this, and it has several locations, or you could go to The Wieners Circle in Lincoln Park or Superdawg. Let me know if you have another favorite place! Do not—I repeat, do not—ask for ketchup.

77. Slice into a Chicago deep-dish pizza.

People who haven’t had this don’t understand how, well, tall it is. This is one of those foods that sometimes weirds out people from other countries. I don’t know why. What’s weird about an entire pound of cheese on a pizza slice? Just keep in mind that if you and a friend decide to split a small one, you’re going to be stuffed. My favorite is the spinach from Giardano’s (multiple locations.)

78. Try an Italian beef sandwich.

I have to admit this is not my thing, but people love them.

79. Go to The Berghoff (but you’ll need reservations.)

I went to this restaurant with my family when I was a kid, and back then I thought it was very ritzy. It’s not actually that ritzy, but very nice: a German restaurant that’s been in operation since 1898.

80. Pick up a tin of Garrett’s Chicago mix popcorn.

Garrett’s has shops in nine countries, but they call Chicago home. “Chicago mix” is cheese popcorn and caramel corn mixed together, and it’s dangerously addictive. If you’re visiting and you want to bring a gift home to someone, one of the tins decorated with the skyline of Chicago is perfect.

81. Try a Chicago-Puerto Rican original: the jibarito!

I’m putting this on the list as a reminder to try it myself. It’s an invention at Papa’s Cache Sabroso: a sandwich where fried plantains take the place of the bread.

82. Eat at the legendary Billy Goat Tavern.

You can learn about the famous Billy Goat Curse on the Cubs—which was obviously broken in 2016, allowing them to win the World Series—as you eat at the place memorialized in a vintage Dan Ackroyd and John Belushi SNL skit (“no Pepsi!”)

83. Enjoy high tea at the Drake Hotel.

I have a quibble here: didn’t “high tea” originally refer to a more complete meal later in the day, with things like potatoes and kidney pies? I guess somewhere along the way, the meaning changed into “fancy tea,” and at Palm Court at the Drake Hotel, it’s very fancy.

84. Enjoy tapas at Cafe Ba-Ba-Ree-Ba!

This is less famous than everything else on here, but I have to recommend it. We loved this Lincoln Park restaurant twenty-five years ago and we love it today. You order a couple of rounds of tapas, you linger over your meal longer, and you enjoy it more without actually eating too much. The outdoor seating is lovely. It’s good for any meal, and not too crowded for brunch. Sometimes I worry that places like this will be uncomfortable since I don’t drink alcohol, but they don’t mind at all if you’re drinking iced tea or diet Coke instead of sangria.

85. Have a beer at Goose Island Brewery.

Even though I don’t drink, this is a pretty famous Chicago beer, so it made the list! The Brewery and Taproom are on Fulton Street, or you can sit down and have a meal at the Clybourn Brewhouse.

Things for Sports Fans to Do in Chicago

…besides the aforementioned Cubs and White Sox games!

86. Go to a Blackhawks game at United Center.

This is actually on my list of life goals, not because I’m a hockey fan (I don’t even know the rules!), but because I think my love for the song “Chelsea Dagger” will make it a fun experience.

87. Go to a Bulls game at United Center.

While you’re there, take a picture by the Michael Jordan statue.

88. Go to Bears game at Soldier Field.

I may have to update this post in the future, because they probably won’t be at Soldier Field forever. And, fun fact: they might move to a place less than a mile from our house! We’ll see!

89. Enjoy a Big 10 Wildcats sporting event at Northwestern University.

90. Visit the Chicago Sports Museum.

91. Take in a Big East Blue Demons sporting event at DePaul University.

92. Eat at a Harry Caray’s restaurant…

There are a few of them, including Harry Caray’s Tavern on Navy Pier.

93. Enjoy a Chicago-area minor league baseball game.

94. Watch a soccer game at the Globe Pub.

Or football, if that’s what you call it! I bet I’m one of hundreds of thousands of Americans who are taking an interest in this game thanks to Ted Lasso.

95. Go to a Missouri Valley Conference Loyola Chicago Ramblers sporting event.  

A Few More Fun Things to Do in Chicago

95. Go to Joliet Prison.

No, I’m not recommending that you break the law and do hard time. That’s not fun. But you can tour this former prison and historic site, featured in the classic Chicago movie The Blues Brothers.

96. Say hi to some animals at the Brookfield Zoo.

97. Visit the Graceland Cemetery and Arboretum.

I’ve heard it’s really lovely.

98. Enjoy live theatre!

Chicago has an amazing theatre scene, including serious plays and comedy at Second City.

99. Cultivate your music appreciation at the Chicago Lyric Opera.

I love opera. But even if you don’t, you might love going to one here. The opera house is beautiful, the company is world-class, and there are subtitles right by the stage so you always know what’s happening. The costumes and the sets are so sumptuous, and it’s a spectacle you’ll never forget.

100. Contemplate the universe at the Adler Planetarium.

I’m ending on a high note here. This is actually one of my favorite things on the list!

With this post, we’ve actually inspired ourselves to do many more fun things in Chicago!