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50 Things To Do in Chicago

Chicago is home to so many wonderful spaces and places! Here are our 50 favorite Chicago destinations.

  1. Ride the CTA Holiday Express! Each year, the CTA places this festively decorated train on different lines throughout the regular CTA routes. See if you can catch it!

  2. Take a walk along the lake front.

  3. Go to a Chicago sporting event! The White Sox, Cubs, Bears, Fire, and Blackhawks all have games, depending on the season.
    It's a great time, and tickets are easier to get than you might think.

  4. Submit an entry to the IIT Business Idea Challenge.

  5. Design a T-shirt for Threadless. This Chicago based website has unique T-shirts whose designs come from customer submissions.

  6. Play in the Crown Fountain at Millennium Park!
    This unique water feature has two giant towers made out of glass blocks with screens that display huge faces. It's a popular destination in the summer.

  7. Fly a kite in Grant Park.

  8. Catch the flying water droplets along the escalators at Water Tower Place.

  9. Organize and/or participate in a beach clean-up event.

  10. Visit the Oriental Institute at the University of Chicago, a museum dedicated to the study of the ancient Near East. Founded in 1919, it is internationally recognized for its work and collection.

  11. Eat Chinese food in Chinatown, Greek food in Greektown, and Indian food at Devon Street all in the same day!

  12. See at least one movie at the Chicago Outdoor Film Festival. It's like a drive-in for pedestrians that shows classic movies. Bring a cooler and a blanket!

  13. Attend either the New Year's Eve or Independance Day gatherings in Grant Park! 

  14. Successfully organize and/or participate in an IIT Pumpkin Launch Team.

  15. Take a Chicago River Architecture Tour! There are several companies that offer both historical and architectural tours. This is a great way to see the river and enjoy Chicago's unique history and architecture.

  16. Go to the Lincoln Park Zoo! This zoo offers free admission and is open every day of the week.

  17. Take the Yellow Line on the CTA! Not many city-dwellers ride this far-north line, unless they're are heading out to Skokie.

  18. Go to Lake Michigan when it's below zero! Chicago has a beautiful lake front even when it's cold out. The lake looks like an extra-terrestrial landscape with all the ice and water vapor.

  19. Go to the Northwestern University Dearborn Observatory! The Observatory is open to the public on Fridays from 8:00-10:00pm.

  20. Attend the St. Patrick's Day Festival at the Chicago River-the City colors the river green!

  21. Go see the Navy Pier Fireworks! Navy Pier displays fireworks twice weekly from Memorial Day to Labor Day.

  22. Shop on the Magnificent Mile (north Michigan Avenue) and State St. in the Loop. World class shopping is just a bus ride away!

  23. Watch a 33rd St. Productions performance! 33rd is IIT's theatrical production company, and they produce several shows a year.

  24. Visit a museum while they offer free admission! Chicago boasts some great museums, and they offer free admission several times a year.

  25. Go to the Improv Olympics! Located in Wrigleyville, this hilarious improv production company and school has inexpensive shows that make for a great night out!

  26. Go see the Chicago Symphony Orchestra! They offer student tickets for $10, an absolute bargain for world-class music.

  27. Host a student for Interview Weekend.

  28. Go to Vosges Haut Chocolat! This gourmet chocolate and truffle shop off the Armitage stop on the Brown Line has top-notch chocolate, and the store offers free samples of all their products.

  29. Visit the Frank Lloyd Wright Home! The home and studio that famous architect Frank Lloyd Wright lived in for over 20 years is open for tours, and is a great stop for anyone who loves architecture.

  30. Visit the Willis Tower Sky Deck! The tallest building in the western hemisphere boasts an awesome view of not only the city of Chicago but 4 other states!

  31. Walk around the South Loop in the morning to smell the chocolate in the air! A chocolate factory in Chicago that produces cocoa powder makes the area around the building smell like brownies.

  32. Listen to a live musician perform on the Green line train!

  33. Hear a joke told by Prof. John Twombly of the Business Department.

  34. Slide down the base of the Picasso statue in Daley Plaza!

  35. Take a picture of you "pushing" the Trump Tower!

  36. Participate in the "Hustle Up the Hancock"! This is an annual event where people run up the stairs in the John Hancock building to raise money for lung cancer research.

  37. Go to the Chicago Auto Show at McCormick Place! If you love cars, this is the place for you. Started in 1901, the Chicago Auto Show is the largest auto show held in North America.

  38. Go to Looptopia, an artistic and cultural program in Chicago's world famous Grant Park!

  39. Visit the Taste of Chicago! Many restaurants gather in Grant Park to showcase what they have to offer, with live music and entertainment! 

  40. Participate in the Chicago Polar Plunge! This annual event is not for the faint of heart--joining the Chicago Polar Bear club requires you to jump in a freezing cold lake Michigan for at least 30 seconds!

  41. Attend the Sophomore Leadership Retreat! Learn about yourself and how to be a leader at this annual retreat for second year IIT students.

  42. Watch the whales and dolphins from the outside of the Shedd Aquarium at night! 

  43. Take someone special to the Alfred Caldwell Lily Pool! This is easily one of the most romantic spots in Chicago, especially in the summer.

  44. Check out the waterfall on the lakefront path at McCormick Place!

  45. Be a trapeze artist for a day! Go to the Flying Gaonas Gym. This 7th generation circus family will teach you how to be a real trapeze artist! Classes are offered from beginner to advanced.

  46. Go to Giordano's Pizza in Prudential Plaza! Make sure to order stuffed pizza, and try to get a table under the glass ceiling (especially when it's raining)!

  47. Go to Hot Doug's on California and Roscoe. The Sausage Superstore and Encased Meats Emporium allows you to enjoy exotic hot dog options like Antelope and Spicy Crocodile. Cash only, so be prepared.

  48. Go ice-skating in McCormick Plaza in the winter! Skating is free, and you can rent skates for $10.

  49. Try to take the most unique picture of Cloud Gate. One of Chicago's most recognizable landmarks, Cloud Gate (or the Bean as it's commonly called) offers a great opportunity for unique photography!

  50. Go to Chinatown, a short walk from IIT's main campus.