Chicago is known as Second City, but there are plenty of first-rate attractions—from Michelin-starred restaurants and historic cocktail dens to world-class museums and golden-sand beaches—to make your visit a memorable one. You could go full-on tourist and climb to the top of the Sears—ahem, Willis—Tower to stand on a glass platform 1,353 feet in the air for the ultimate bird’s eye view, or shop the big brand stores on the Magnificent Mile, but there’s much more to the Windy City than that. To help you make the most of your trip, we’ve rounded up 11 of the best things to do in Chicago.
Restored by former Hollywood set designers Robin Standefer and Stephen Alesch of Roman and Williams Buildings and Interiors, the city’s coolest hotel, in an 1893 gentleman’s sporting club, is more than just a place to stay. A dimly lit, wood-paneled game room is studded with pool, checkers, chess, and shuffleboard tables for booze-fueled play into the wee hours—there’s even a bocce court lined with oyster shell fragments—and upstairs, the rooftop terrace at Cindy’s serves the best brunch in town, with a view of Millenium Park to match.
If you want to visit Chicago’s first craft-cocktail den, you’ll need to follow some house rules, among them no cell phones, no baseball hats, no cosmos. But those who find the decade-old Bucktown speakeasy’s secret entrance behind a colorful wall mural will be rewarded for their obedience. The interiors look like a Victorian salon by way of Paris, with opulent gray curtains against the blue backdrop, crystal chandeliers, and modernist leather wingback chairs, and the artisanal, pre-Prohibition drinks are transcendent. Coming with a group? Ladle-up the brandy- and scotch-infused Violet Hour Punch No. 6.
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No trip to Chicago would be complete without a souvenir selfie taken in front of Anish Kapoor’s iconic Cloud Gate statue, also known as The Bean, near the entrance to Millenium Park. But those who venture farther into Grant Park’s most famous square will be rewarded with plenty of other amusements. In the summer, the hulking steel-covered bandshell at the Frank Gehry–designed Jay Pritzker Pavilion plays host to a bevy of alfresco opera and symphony performances, and headlining artists like Arcade Fire and The Killers, take the stages at the annual Lollapalooza Festival.
A leisurely boat tour is perhaps the best way to survey the city’s impressive architectural legacy, which includes works by pioneering modernist designers such as Mies van der Rohe and Bertrand Goldberg. Don’t have your sea legs? Walking tours led by the Chicago Architectural Foundation start at the Riverwalk, a 1.3-mile-long stretch along the Chicago River that is dotted with outdoor cafés and restaurants and offers some of the best views in the city.
Forget the deep-dish pizza and giardiniera-topped sausages—though, a case can always be made for sampling a city’s fast food with gusto. If you have only one meal here, beeline to Lincoln Park for the three Michelin-starred cuisine concocted by Grant Achatz at Alinea, one of the world’s best restaurants. The dining room was renovated last year with Parisian inspired influences (think velvety banquettes and ornate architectural molding) that make it almost as pretty as the avant-garde dishes that arrive at your table—lamb loin with blackberries and black garlic, Japanese icefish with fermented kumquat sauce. Almost.
Tina Fey, Bill Murray, Steve Carrell—they all got their start at the legendary comedy venue The Second City, so the odds of seeing a future Saturday Night Live cast member are in your favor. Go for a show or sign up for a one of their three-day improvisational intensives, which can help you unearth your inner comedian through a series of unexpected group prompts.
Chicago’s answer to New York City’s High Line, the 606 is an elevated park trail on a converted railway line that draws locals and visitors alike. The path connects Northside Chicago neighborhoods from Bucktown to Humbolt Park, and interactive works by local artists span its length. The best way to see it all? Rent a Divvy bike for the day, then hit the pavement. There are plenty of places to pull off along the way for a mid-day snack.
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Charlie Chaplin and Frank Sinatra drank here. So did Al Capone—in fact, Scarface likely made use of a trapdoor behind the bar that led to secret underground tunnels for a quick getaway. The 1907 bar was a Prohibition-era hangout for mobsters and gamblers, but it was also the place for the best jazz in town. Billie Holiday, Tommy Dorsey, and Benny Goodman all played at the Green Mill, and the club continues to draw musical legends, making it more than worth the cab ride out of the way to Uptown.
A dinosaur named Sue—the largest, most complete T-Rex skeleton on the planet—greets visitors at the north entrance to The Field, where you can explore the 5,000-year-old rooms of a reconstructed Egyptian tomb and walk through a stunning recreation of an 1800s Native American earth lodge. The museum also houses some 30 million objects, from natural history specimens to anthropological collections, many of which were part of the exhibits on display during the 1893 World’s Columbian Expo. (You can see more history from the Chicago World’s Fair at the Museum of Science and Industry, 10 minutes away.)
Given all of the attention paid to the River and the skyline, it’s easy to forget that Chicago is actually something of a beach town. In the summer, the shores of Lake Michigan are teeming with sun worshippers with varied interests. North Avenue is best for people watching, as it’s the city’s most popular beach. Those looking for deep-water swimming opt for Oak Street, and Ohio Street enjoys calm waves and spectacular downtown views. Seeking a little peace and quiet? Head to the South Side.
Seeing one of baseball’s last manual scoreboards in action makes a trip to Wrigley Field worth it. Couldn’t snag a ticket to the big game now that the Cubs are World Series champs? Wannabe statisticians and sports commentators can’t leave the Windy City without a trip to Wrigleyville, the always-buzzing assemblage of bars, beer gardens, and restaurants that surround the iconic 103-year-old stadium. Make your way to divey Nisei Lounge, a 1951 stalwart where you can play darts between innings.