Chicago Summer Vacation/Staycation Ideas!

In no particular order…


  1. Navy Pier (MORE HERE!)
  2. Adler Planetarium: $10/$6
  3. Chicago Architecture Foundation Tours:
  4. Second City
  5. Bowling
    1. 10Pin
  6. Millennium Park
    1. Pritzker Pavillion and steel-ribbon bridge
    2. Cloud Gate (aka “The Bean”)
    3. Crown Fountain
    4. Park Grill Restaurant   VIDEO
  7. Pepsi Tall Ships:
  8. Chicago Cubs Game
  9. Chicago White Sox Game
  10. Kayak
  11. Chicago Cultural Center
  12. If it’s May- you can check out the tulips on the Magnificent Mile!
  13. Dinner tour
  14. Take a picnic to The Great Lawn in Millennium Park
  15. Wine tour
  16. Check out a local museum
    1. The Peggy Notebaert Nature Museum: ($6-$9)
    2. Chicago History Museum
  17. Fix any kind of sweet tooth with a candy store
    1. Candyality
    2. Hershey’s
  18. Skydive
  19. Pick up a “Go Chicago Card” and see how much you can see in a day or a few days
  20. Shop Michigan Avenue
  21. Shop State Street
  22. Boating
  23. Jet skis
  24. Volleyball
  25. Green City Market:
  26. Overnight at The Field Museum!  Doze with the Dinos:
  27. Single at The Brookfield Zoo June 25:
  28. City Lights Bike Tour:
  29. Chef Class at Kendall College:
  30. Visit Networld at The Museum of Science and Industry:
  31. Attend a convention
  32. Take a tour from the comfort of your home online:
  33. Maxwell Street Market on Sundays:
  34. Broadway in Chicago: Billy Elliot
  35. See what’s playing at the Chicago Theatre (My Conan video)
  36. Shoreline Sightseeing
  37. IMAX
  38. Bike Chicago
  39. Tall Shop Windy
  40. Lincoln Park Zoo
  41. Take and architecture tour
  42. Ride the Chicago Trolley and Double Decker
  43. Museum of Science and Industry
  44. John Hancock Observatory
  45. Sky Deck Ledge at the Willis Tower
  46. Segway tour
  47. Chicago water taxi
  48. Blue Man Group
  49. Take the 3 hour drive to Wisconsin Dells and enjoy a relaxing stay at Rhapsody Resort and Spa!
  50. Take a tap class
  51. Experience Maxwell Street Market every Sunday
  52. Learn at Millennium Park’s Lurie Garden (FREE!)
  53. Lincoln Park Conservatory (FREE!)
  54. Chicago Botanic Garden
  55. Downtown Farmer’s Market


Jen Knoedl is Executive Producer of JenChicago Productions, as well as its enthusiastic video host. Click here to find out about sponsorship and partnering opportunities regarding travel, Chicago and entrepreneurship. Tweet Jen at @JenTravelsLife

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