Gallery-goers flock to the Art Institute of Chicago (111 South Michigan Ave.) for its brilliant mix of preserved and modern art. From 18th century Japanese prints to studies of 20th century architecture and design to video installations by renowned living filmmakers, the AIC (one of Trip Advisor’s top-ranked museums for four years running) covers artistic endeavour on a global scale. General admission tickets from $14, available online.
If you’re in need of a selfie that screams Chicago, look no further than Millennium Park (Michigan and Columbus Avenues), where you can pose in front of Anish Kapoor’s iconic “Cloud Gate” (known colloquially as “The Bean”). With 25 million annual visitors, Millennium isn’t the kind of park where you’ll find much solitude, but with its vast collection of public art, proximity to the waterfront and free live music, it’s somewhere you’ll want to be for at least part of your trip to the Windy City. Free.
One of the best ways to take in Chicago’s sights is from the deck of a boat in the city’s eponymous river. Architecture and history fans can hop aboard the Chicago Architecture Foundation River Cruise for an informed take on more than 50 iconic buildings in the city that invented the skyscraper. Tickets from $46, available online.
Of course, if you prefer the view from above, head to the Skydeck (233 South Wacker Dr.)—the highest observation deck in the U.S.—where you can spy 50-mile views of Chicago from the 103rd floor of the Willis Tower (formerly Sears). Adventurous visitors to the Skydeck can tiptoe out into The Ledge’s glass-bottomed boxes, which allow for unfettered—and unnerving—views of the city below. Tickets from $23, available online.
If the idea of a “garage turned honky-tonk taco shack” appeals to you, slide on over to Big Star (1531 N Damen Ave.) for a fiesta of Mexican-style street grub, cold craft beer and a cocktail list that’ll make your head spin.
Who visits the greatest pizza city on earth and neglects to bite into a deep-dish pie? Not you. Pack your appetite (and a bottle of Tums) and head out to Lou Malnati’s (439 North Wells Street), a Chicago institution where you’ll find thick and cheesy deep-dish delights served on a buttery crust.
Jazz aficionados won’t want to miss a night out on a night at The Green Mill (4802 N. Broadway Ave.). Sure, it’s where Al Capone and his henchmen once kept a booth (and eyes on both doors) but it’s a Chicago legend in its own right, with live jazz every night laid down in a funky venue where the music plays well past last call.
For a creative escape from the downtown core, head west to Wicker Park. Known for its music scene, fashion boutiques, cafés and cutting-edge restaurants, this eclectic neighbourhood is the ideal spot for culture vultures on the prowl. While you’re there, take a stroll on The 606, an elevated rail line that’s been converted into 2.7 miles of urban green space.
In the mood for a little shopping therapy? Pack up the credit cards and head over to the Magnificent Mile, an upscale stretch of North Michigan Avenue with retailers ranging from Burberry and Louis Vuitton to Banana Republic and The Gap. Packed with charming cafés, top-notch restaurants and towering shopping malls, the Magnificent Mile is where you want to be if you’ve got a spending itch to scratch.