Chicago To-Do List

15 things you have to do during your time in Chicago.

By Deepti Sailappan, Managing Editor ('19-'20)

  1. Watching a Cubs game is probably a Chicago rite of passage. Head to Wrigley Field to experience fans’ unparalleled passion, which (following the beloved Cubbies’ 2016 World Series win) has never been fiercer. Tickets start around $14.
  2. The Art Institute of Chicago in the Loop lends itself to nearly infinite exploration. Since the museum is free with your student ID, one approach is to tackle just two exhibits per visit: Impressionist and Islamic art, for example, or Japanese and medieval art. Afterward, stop by the stone lions outside the museum to watch the ever-present drummers nearby.
  3. Millennium Park, adjacent to the Art Institute, offers plenty besides photo opportunities at the Bean (real name: Cloud Gate). Catch an outdoor concert in Pritzker Pavilion or wander Lurie Garden. In winter, ice skate below the Bean (free, with skate rentals for $10).
  4. Probe centuries of history at the National Museum of Mexican Art. The free collection here ranges from pre-Columbian masks to subversive contemporary installations, with a striking Day of the Dead exhibition on display every fall. Afterward, grab a snack in surrounding Pilsen; we love the widely sold paletas, decadent popsicles.
  5. Window-shop in Chicago’s hipster quarter, Wicker Park. Browse Myopic Books, a used book paradise, and explore the row of vintage boutiques alongside Milwaukee Avenue. Finish by sampling the inventive ice cream flavors at Jeni’s.
  6. Second City holds mythic status as the training ground for generations of wildly successful comedians. Steve Carell, Stephen Colbert, and Amy Poehler are among the past performers at this Old Town improv theater, launched in 1959 by three University graduates. Tickets to professional performances start at $18, with shows by the theater’s comedy students priced at $12.
  7. Improv Shakespeare in Lincoln Park is another offbeat comedy option. A talented troupe of actors crafts a very loose adaptation of one of the Bard’s plays based on audience members’ suggestions at the start of the show. Tickets are $18.
  8. Museum Campus in the South Loop has something for a vast slate of interests. Scope out Egyptian tombs and the world’s largest Tyrannosaurus rex fossil at the Field Museum ($19 for basic admission), be spellbound by stars at Adler Planetarium ($12 for general admission), or see stingrays and beluga whales at Shedd Aquarium ($20 for general admission). Free admission days for Chicago residents throughout the year are listed on the museums’ websites.
  9. Gobble your way through Chinatown. Bubble tea from Chatime or Joy Yee pairs fabulously with the cheap, tasty custard buns and sesame balls at Saint Anna Bakery. Alternatively, sit for a dim sum dinner at one of the neighborhood’s many excellent restaurants. If your appetite can handle it, try the rolled ice cream at Legend Tasty House for dessert.
  10. Walking along the Chicago River is lovely in fall and spring. People-watch, spot friendly dogs, and admire the awe-inspiring skyscrapers. Examine the surface of the Tribune Tower: it features carefully labeled rocks from famous places, from the Forbidden City to the moon. The area is especially vibrant around Saint Patrick’s Day, when the river is dyed green to celebrate.
  11. After Thanksgiving, Christkindlmarket transforms Daley Plaza in the Loop into an antique village inspired by the 16th-century Christmas market in Nuremberg, Germany. Vendors sell glass ornaments and whimsical clocks alongside hot chocolate and strudel in a magical setting. Entry is free.
  12. Lincoln Park Zoo is free and enormous, with animals from aardvarks to zebras, gorillas to penguins. Seasonal events include ZooLights, a Christmas festival that opens in late November.
  13. Plan a beach day during spring quarter. While the Point is gorgeous, Chicago’s lakefront is strewn with bustling beaches. Local favorites include North Avenue Beach in Lincoln Park and Oak Street Beach near the shopping of Chicago’s Magnificent Mile.
  14. Experience the thrills of a street festival. Summer is packed with concerts and block parties, but a slew of events occur during the year, too—from Chinese New Year around the city to the Columbus Drive artists’ parade in October.
  15. Dig into deep-dish pizza, the city’s cheesy and decadent signature dish. Giordano’s, which has several locations around Chicago, is the most convenient place to grab a classic stuffed pie.