By Avery Newmark
The Atlanta Journal-Constitution
Looking for an easy city escape this spring? Chicago is just a quick flight from many American cities, often at surprisingly affordable rates. You'll touch down in a city bursting with incredible art, amazing food, and experiences straight out of your favorite movies.
Here’s how to live your best Chicago weekend this spring.
Bueller? Bueller?
Re-create “Ferris Bueller’s Day Off” with a visit to the Art Institute of Chicago. This museum spans more than a million square feet and is home to masterpieces like Picasso’s “The Old Guitarist” and Grant Wood’s “American Gothic.” For the full Ferris Bueller experience, follow the museum’s official movie tour, which takes you through six key artworks from the film.Next, take in the city from 1,353 feet up at the Willis Tower Skydeck (formerly the Sears Tower), just like Sloan did in the movie. And, of course, no Ferris-style day is complete without catching a Cubs game at Wrigley Field. Built in 1914, this legendary ballpark is where Babe Ruth famously called his shot in the 1932 World Series. After the game, celebrate a Cubs win (fingers crossed) with a drink at one of Wrigleyville’s lively bars.
Float Through History on an Architecture Boat Tour
Yes, it’s touristy. And you may not even be all that into architecture. But this tour is hands down one of the best ways to experience Chicago. You’ll catch one-of-a-kind city views along the river while guides point out architectural gems like the corncob-shaped Marina City towers and the Tribune Tower’s dreamy neo-Gothic design. If you can, opt for an evening tour—the city lights reflecting on the water are nothing short of incredible.Snap a Selfie at “The Bean”
No trip to Chicago is complete without a stop at Cloud Gate—better known as “The Bean.” This massive, mirrored sculpture in Millennium Park distorts the skyline (and your selfie) in the coolest way.
People hang out as Chicago's skyline is reflected in the Cloud Gate sculpture, otherwise known as "the Bean," in Millennium Park on May 15, 2022. Erin Hooley/Chicago Tribune/TNS
Laugh The Night Away at Second City
If you need a good laugh, head to the legendary Second City. This comedy theater launched the careers of Tina Fey, Bill Murray, and Tim Baltz from “The Righteous Gemstones.” Shows run nightly with a mix of improv and sharp sketch comedy.Bite Into an authentic Chicago-Style Hot Dog
Chicago takes its hot dogs seriously. Anthony Bourdain once called them “the finest in the land,” and he wasn’t wrong. Piled high with mustard, pickles, sport peppers, relish, onions, tomatoes, a dill spear. and celery salt—no ketchup allowed—it’s a flavor-packed classic. Grab one at a neighborhood stand or hit up local favorite Superdawg.Swing By The Legendary Green Mill Jazz Club
Cap off your evening with live jazz at the Green Mill, a historic club that was once Al Capone’s go-to hangout during Prohibition. The vibe is old-school cool, the music is top-notch, and if you want the full experience, order a whiskey soda or a local beer—this isn’t a craft cocktail kind of place.Copyright 2025 The Atlanta Journal-Constitution. Visit at ajc.com. Distributed by Tribune Content Agency, LLC.
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