99 Things To Do in Chicago

99 Things To Do in Chicago

Oh Chicago.

Sweet home, Chicago.

How do I love thee?

You go by many names (Windy City, Second City, Chi-town, the Heart of America, “my kind of town”).

And you have many facets.

You’re never the same city from year to year.

And despite your notorious reputation, you prove time and time again that you are one of the world’s best cities to have FUN in.

Oh Chicago, I love you. For all your ups and downs.

And I’ll always be proud to call you home.

99 Things To Do in Chicago

1. Walk Through the Cloud Gate

2. Have a Beer at Wrigley Field

3. Walk the 606

4. Watch the Sunrise Over Lake Michigan

5. Visit the Miniature Thorne Rooms at The Art Institute

6. See ‘Sue’ the T-Rex at the Field Museum

7. Have a Burger at Au Cheval

8. Take a #shoefie at the Skydeck

9. Walk the new Chicago Riverwalk in Summer (or Winter)

10. Have Cocktails on the 96th Floor of the John Hancock

11. Shoot in front of the Flamingo Rum Club (one of My Favorite Shooting Locations in Chicago)

12. See an Opera at the Lyric Opera (even better if it’s Opening Night!)

13. Have Drinks By the Fireplace at RL

14. Try the Crab Cakes at Gibson’s

15. Watch the Chicago River Turn Green for St. Patrick’s Day

16. Visit the University of Chicago Library

17. Have a Coffee at Sawada

18. Do Dim Sum in Chinatown

19. Walk to the Lighthouse at North Avenue Beach

20. Have Pizza Pot Pies at Chicago Pizza & Oven Grinder Co.

21. See a Performance at Second City

22. Eat Authentic Greek Food in Greektown (Greek Islands is my favorite!)

23. Try An Old-Fashioned Doughnut from Doughnut Vault

24. Wander the Green City Market in Summer

25. Hunt for Your Perfect Dream House among the Beautiful Mansions of the Gold Coast

26. Make Your Own Tornado at the Museum of Science & Industry

27. Visit the Fairy Castle at the Museum of Science & Industry too

28. Try Afternoon Tea at The Allis

29. Have Drinks on the J. Parker Rooftop

30. Visit the Museum of Contemporary Art

31. Get A Massage At The Peninsula (or Stay the Night)

32. Take the ‘El’ Through the Loop

33. Wander the Garfield Park Conservatory

34. Wander the Christkindl Market At Christmas

35. See the Flamingo

36. See the Stars at the Adler Planetarium

37. Try the Scrambled Eggs at 3 Arts Club Cafe

38. Shoot at the Marina Towers

39. Get Rosé Slushies at Expat

40. Spend at Afternoon Wandering the West Loop

41. Have Drinks at The Gage

42. See Buckingham Fountain

43. Visit the Tribune Tower

44. Drive Out to the Morton Arboretum

45. Get an Angel Food Muffin at Beatrix

46. Attend a Concert at Ravinia

47. Visit the Lion’s Den at the Lincoln Park Zoo (it’s always free admission!)

48. Slurp Oysters at Publican

49. Listen to Jazz at The Green Mill

50. Attend Lollapalooza At Least Once

51. Eat Sushi at Kai-Zan

52. Try Garrett Popcorn (if you’re feeling touristy)

53. Spend a Sunday at the Shedd Aquarium

54. Shoot a Photo at Lincoln Park’s Honeycomb

55. Get a Rainbow Cone at Rainbow Cone

56. Ride the Ferris Wheel at Navy Pier

57. Have Tiki Drinks at Lost Lake

58. See A Concert at Soldier Field (I saw Beyoncé last year and it was ahhhhmazing)

59. Visit the Chicago History Museum

60. Boat Ride Down the Chicago River

61. Do Brunch at Mindy’s Hot Chocolate

62. Explore Unique Cocktails at The Violet Hour (Then Get Tacos Across the Street at Big Star)

63. Brave the Crowds on Michigan Avenue (My 7 Favorite Stops)

64. Have at Least One Meal at avec

65. See the Tiffany Domes at the Chicago Cultural Center

66. Roast Marshmallows at Promontory Point

67. Try a Chicago-Style Hot Dog

68. Shop at American Science & Surplus

69. Order Tacos at Antique Taco

70. See a Play at the Shakespeare Theater

71. Have a Late-Night Binge Meal at Portillo’s

72. Take a Chicago Architecture River Cruise

73. Get the Prohibition Sauce at Twin Anchors

74. See a Show at the Chicago Theatre

75. Try the Gobi Manchurian at Rangoli

76. Have a Drink at Cindy’s

77. Get Authentic Asian Groceries at Joong Boo Market

78. Have a Picnic in Humboldt Park

79. Get a Cookie at Summer House Santa Monica

80. Kiss at the Obama Kissing Rock

81. Have Dinner at Parachute

82. Order Hash at Southport Grocery & Cafe

83. Visit the Confederate Mass Grave (the largest mass grave in the Western Hemisphere)

84. Shop at Brown Elephant Resale

85. See a Concert at Millennium Park

86. Walk the Chicago Lakefront Trail by the Shedd Aquarium

87. Read a Book at the Harold Washington Library

88. Have an Innovative Ice Cream at Jeni’s

89. Attend the Old Town Art Fair

90. Ice Skate in Front of the Cloud Gate in Winter

91. Visit a Frank Lloyd Wright House

92. See the Bulls Play At the United Center

93. Have Drinks on a Rooftop in Summer (See My Favorites in My Chicago Travel Guide)

94. Ride the Carousel at the Lincoln Park Zoo

95. Visit the Museum of Contemporary Photography

96. Head to Devon Avenue for Indian Thali Plates

97. Do Brunch at Oyster Bah

98. Order Mashed Potato Pizza at Piece Pizza

99. Watch a Firework Show at Navy Pier

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