75 Best Things to Do in Chicago

Chicago, the Windy City, is bursting with world-class attractions, stunning architecture, vibrant neighborhoods, and endless activities for all types of travelers. Whether you’re visiting for the first time or you’re a local looking for fresh ideas, this guide of 75 things to do in Chicago has you covered!

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1-10: Iconic Attractions

1. Skydeck Chicago: Stand on the glass ledge at Willis Tower for breathtaking views.
2. 360 Chicago Observation Deck: Admire panoramic cityscapes from the John Hancock Center.
3. Cloud Gate (The Bean): Take a selfie with this iconic reflective sculpture in Millennium Park.
4. Chicago Riverwalk: Enjoy scenic views and waterfront dining along the river.
5. Navy Pier: Ride the Ferris wheel, shop, and catch stunning lakefront views.
6. Art Institute of Chicago: Explore masterpieces like "American Gothic" and "The Bedroom."
7. Field Museum: Marvel at Sue, the most complete T. rex ever discovered.
8. Shedd Aquarium: Discover aquatic wonders from around the world.
9. Museum of Science and Industry: Explore hands-on exhibits and a real U-boat.
10. Adler Planetarium: Gaze at the stars and learn about the cosmos.

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11-25: Outdoor Adventures

11. Lincoln Park Zoo: A free zoo perfect for families and animal lovers.
12. Grant Park: Relax in this sprawling urban green space.
13. Lakefront Trail: Walk, bike, or run with stunning views of Lake Michigan.
14. Garfield Park Conservatory: Stroll through lush gardens and exotic plants.
15. Maggie Daley Park: Enjoy whimsical playgrounds and ice skating in winter.
16. Buckingham Fountain: Admire one of the largest fountains in the world.
17. Oak Street Beach: Soak up the sun along the lakefront.
18. Chicago Botanic Garden: Explore serene gardens and blooming landscapes.
19. Ping Tom Memorial Park: A peaceful escape in Chinatown.
20. Chicago River Kayaking: Paddle through the heart of the city.
21. Lurie Garden: A hidden gem in Millennium Park.
22. Humboldt Park: Experience Puerto Rican culture and beautiful lagoons.
23. Promontory Point: Enjoy a picnic with unbeatable skyline views.
24. Montrose Beach: A family-friendly beach with sand volleyball courts.
25. Jackson Park: Explore the historic park with a Japanese garden.

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26-40: Foodie Adventures

26. Deep-Dish Pizza: Indulge at Lou Malnati’s, Giordano’s, or Pequod’s.
27. Chicago-Style Hot Dogs: Try a classic at Portillo’s or a local stand.
28. Revival Food Hall: Sample dishes from local chefs in one spot.
29. West Loop Restaurants: Explore the city’s hottest dining district.
30. Garrett Popcorn: Snack on the famous Chicago mix.
31. Chinatown’s Dim Sum: Savor authentic Chinese cuisine.
32. The Violet Hour: Sip cocktails at this hidden speakeasy in Wicker Park.
33. Taste of Chicago: Visit during summer for the nation’s largest food festival.
34. Maxwell Street Market: Sample tacos, tamales, and more at this Sunday market.
35. Italian Beef Sandwiches: A must-try Chicago classic.
36. Green City Market: Shop fresh produce and local goods.
37. Chicago Craft Breweries: Visit Goose Island or Revolution Brewing.
38. Ethnic Neighborhoods: Explore authentic cuisines in Little Italy, Greektown, and Pilsen.
39. Steak Houses: Treat yourself at Gibson’s or Chicago Cut Steakhouse.
40. Chicago Pizza and Oven Grinder Co.: Don’t miss their famous pizza pot pie.

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41-55: Arts, Culture, and Entertainment

41. Chicago Theatre: See live performances at this iconic venue.
42. Second City Comedy Club: Laugh out loud at world-class improv.
43. Museum of Contemporary Art: Discover rotating modern art exhibits.
44. Wabash Arts Corridor: Admire vibrant street art and murals.
45. Steppenwolf Theatre Company: Catch a critically acclaimed play.
46. Pilsen Murals: Explore colorful murals and Mexican culture.
47. Lyric Opera of Chicago: Experience a night of grandeur and music.
48. Chicago Symphony Orchestra: Enjoy classical music at its finest.
49. SummerDance Festival: Join the city’s free outdoor dance parties.
50. Music Box Theatre: Watch indie and classic films in a historic cinema.
51. Chicago Cultural Center: Attend free events and exhibitions.
52. Chicago Blues Clubs: Visit Kingston Mines or Buddy Guy’s Legends.
53. Andersonville: Explore this artsy neighborhood with eclectic shops.
54. Old Town School of Folk Music: Attend concerts and classes.
55. Maxwell Street Blues: Experience live music and soulful performances.

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56-75: Unique Experiences

56. Architectural Boat Tour: Learn about the city’s iconic buildings.
57. Wrigley Field: Catch a Cubs game or tour the historic stadium.
58. United Center: Watch the Bulls or Blackhawks in action.
59. Chicago Air and Water Show: See thrilling aerial stunts during summer.
60. Fireworks at Navy Pier: Enjoy free summer night shows.
61. Chicago Water Taxi: Get around the city via the river.
62. Chicago History Museum: Dive into the city’s rich past.
63. Lincoln Park Conservatory: A peaceful retreat with exotic plants.
64. Driehaus Museum: Step into Gilded Age elegance.
65. Shakespeare Theater: See a performance on Navy Pier.
66. Frank Lloyd Wright Homes: Tour his famous Oak Park designs.
67. Green Mill Cocktail Lounge: A legendary jazz bar with a 1920s vibe.
68. DuSable Museum: Explore African American history and culture.
69. Peggy Notebaert Nature Museum: Perfect for families and nature lovers.
70. Chicago’s Haunted Tours: Dive into spooky stories and history.
71. South Side Murals: Discover stunning public art.
72. Vintage Shopping: Browse unique finds in Wicker Park.
73. Chicago Sports Museum: A fun stop for sports fans.
74. Day Trip to Starved Rock State Park: Escape to hiking trails and waterfalls.
75. Try Windy City Sweets: End your trip with a sweet treat.

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With so much to see and do, Chicago offers something for everyone. Whether you’re a foodie, history buff, nature lover, or adventure seeker, you’ll never run out of things to explore in this vibrant city. Start planning your trip today and make memories that last a lifetime!