30 Things to Do in Chicago

My husband and I have visited Chicago before, but we recently took our two boys, who are 6 and 9. Their verdict? Coolest City Ever. It’s kinder than New York, still with the buzz, energy, culture and cuisine of a world-class city. Most believe The Windy City is named for the unforgiving cold breezes off Lake Michigan in winter, when in fact it’s an 1890 reference about local politicians being full of hot air. Chicago is also called Second City, after it literally rose from the ashes following the devastating 1871 fire to become a world showcase for design and architecture.

  1. Getting a selfie in Millennium Park at “The Bean,” the reflective Cloud Gate sculpture.

  2. Walking over Frank Gehry's artsy BP Bridge to Maggie Daley playground, an incredible space with creative play equipment, an enchanted garden, slides, swings and more!

  3. Renting rollerblades from the Maggie Daley Field House and cruising around the park.

  4. Going to Stan’s for coffee and doughnuts that almost look too good to eat—almost!

  5. Catching that Broadway show you’ve been dying to see in the Theatre District.

  6. Sipping old-fashioned cocktails while admiring the incredible ceiling frescos in the lobby of the Palmer House, the oldest hotel in the United States.

  7. Riding the “L.” Not only do kids love taking the train, it’s cheaper than an Uber/Lyft ride.

  8. Taking a river cruise to admire the architecture then going through the lock system out to Lake Michigan to admire the skyline—and Buckingham Fountain—at night.

  9. Snagging a table at the bar at Gibson’s and tucking into a legendary steak.

  10. Laughing until you cry at Second City, the famous comedy club where Bill Murray, Tina Fey, Amy Poehler, Steve Carell and Chris Farley got their start.

  11. Ducking into the decades-old Exchequer Pub for famous deep-dish pizza and a pint.

  12. Savoring the truffle toast during brunch at the widely acclaimed Monteverde on the West Loop.

  13. Watching the beluga whales at the Shedd Aquarium then watching the awe-inspiring dolphins leap eight feet out of water.

  14. Devouring the creamiest hazelnut gelato at Eataly.

  15. Ordering fried slivers of pig ears at The Purple Pig and surprisingly loving them!

  16. Conquering your fear of heights on the Tilt attraction at the 360 Chicago Observation Deck (100 stories high) or the Skydeck at Willis Tower (110 stories high).

  17. Playing interactive games and seeing rare memorabilia at the Chicago Sports Museum.

  18. Pub-crawling around Wrigleyville then catching a Cubs game at Wrigley Field.

  19. Shopping the trendy galleries and boutiques in Wicker Park.

  20. Browsing the incredible designer names at The Magnificent Mile and wishing you had $500 to spend on tennis shoes.

  21. Sampling the amazing popcorn at Garrett’s that tastes as good as it smells.

  22. Listening to incredible jazz at The Green Mill.

  23. Getting free admission into the 35-acre Lincoln Park Zoo, one of the oldest zoos in the country.

  24. Enjoying innovative Mexican cuisine at the Rick Bayless landmark Frontera Grill.

  25. Spending half a day with your jaw dropped at the Picasso’s, Van Gough’s, Hopper’s and Seurat’s at the Chicago Institute of Art.

  26. Visiting the Museum of Science and Industry, one of the only remaining structures of the Chicago World Fair constructed in 1893. (Plane ride read: Devil in the White City)

  27. Riding the Ferris wheel at Navy Pier, in the city where the world’s first Ferris wheel premiered during the World’s Fair by George Ferris.

  28. Stimulating your brain at the Field Museum, which houses 40 million artifacts and specimens.

  29. Taking the short trip to Oak Park to see the house and studio of Frank Lloyd Wright. (Plane ride read: Loving Frank)

  30. Finding your inner Ferris Bueller and relishing your day in Chicago.