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50 Things To Do in Chicago

Chicago is home to so many wonderful spaces and places. Here are some of our 50 favorite and unique 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. White Sox, Cubs, Bears, Fire, or Blackhawks.
    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 block 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 it work.

  11. Eat Chinese food in Chinatown, Greek food in Greektown, and Indian food at Devon street all in the same day. One great thing about Chicago is its diverse culinary options. Also check out Korean town and Ukrainian Village.

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

  13. Attend at least one of the following in Grant Park: New Years Eve gathering, Independence Day gathering.

  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 the unique history and architecture.

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

  17. Take the Yellow Line on the CTA.
    Not many city dwellers ride this far north line, unless you 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 dyes the river emerald 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 an bus ride away.

  23. Watch a 33rd St. Productions performance. IIT theatrical production company. They produce several show a year.

  24. Visit a museum when they offer free admission. Chicago boast some great museums, they sometimes offer free admission.

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

  26. Go see the Chicago Symphony Orchestra. They offer student tickets for $10. A bargain for world class music.

  27. Host a student for Interview Weekend.

  28. Go to Vosges Haut Chocolat. This gourmet chocolate 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. Great 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 on a clear you can see 4 states.

  31. Go near the Merchandise Mart 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 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 programming 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. There is live music and entertainment. It's fun for the whole family.

  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 learn 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. Just because the aquarium is closed doesn't mean you can't enjoy it's most acrobatic occupants.

  43. Go to the Alfred Caldwell Lily Pool. 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. One of the many great spots along the Chicago lakefront. IIT's campus is just over a mile away from beautiful lake Michigan.

  45. Be a trapeze artist for a day, go to the Flying Gaonas Gym. This 7th generation circus family will teach you the ins and out of being 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. Go ice skating in the middle of our great city. Skating is free and you can rent skates for $10.

  49. Try to take the most unique picture of Cloud Gate. Quickly becoming one of Chicago's most recognizable landmarks, Cloud Gate or the bean as it's commonly called, offers a great opportunity for a great photo op.

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