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HomeRecreationCity Guides

Chicago

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chi-town, windy city, chicago. the dudes behind whim world show us around the city.

Chicago is home to the largest network of alleyways in North America, weaving together to make up a seemingly infinite number neighborhoods, tucked against the western coast of Lake Michigan. Recreation in Chicago is about pounding the pavement, and the city seems to merit your efforts to explore its finer nooks. From one neighborhood to the next, each of Chicago’s corridors offers its own distinct architectural flavor, driving the vibe of its nearby public spaces and hangout hotspots.

It’s also home to Colin Heaberg and Will Gisel, the eclectic, super-friend duo behind the Whim World entity and Whim Golf: a boutique studio that means to flip the sport of golf and all the age-old associations it comes with on its head. Whim Golf is the pair’s way of challenging “the way it’s always been done” via reimagined corduroy and penny loafers and seersucker.

There’s a certain amount of old school charm mixed with bold experimentalism that Chicago boasts — that of which Heaberg and Gisel have infused into their Whim World ventures. You can read more about the best friends in our recent For Fun™ feature, or read on to see how the duo enjoys the Windy City.

The Concrete Beach

“Concrete Beach” works as a metaphor for the whole city. But in this case, we’re referring to a one mile stretch of curved concrete coastline that, when looking from north to south, sits directly below the Chicago skyline. Officially Concrete Beach is our favorite part of the 18.5 mile long Lakefront Trail, which serves as the premier venue for all things Recreation — especially in the spring and summer months. Recreation takes on all shapes and sizes on Concrete Beach. Bring a towel and work on your tan, go for a jog, rent a bike, dive into Lake Michigan —anything goes. Winter time? Bundle up and test the elements.

Pro-Tip: If you worked up an appetite, stop by the COQ D’OR in the Drake Hotel for some of the city’s finer bar food.

The Art Institute of Chicago

The Art Institute of Chicago is one of the best art museums in the country. It’s a massive building that dominates the eastern side of Michigan Avenue. Collections change often and there’s more art than anyone can digest in a single visit. Some highlights include the Impressionism Wing, including the “Ferris Bueller” painting, the Modern Wing with countless Warhols, and the ancient art from around the world. After you get your art fix, explore Millennium Park and Grant Park nearby. Depending on the day and time of year, there could be anything from a free House Music Festival to an evening outdoor movie screening.

Pro-Tip: Before or after you visit the museum, walk five minutes to see public art sculptures by Jean Dubuffet, Pablo Picasso and Joan Miro.

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Source: Art Institute of Chicago

Wicker Park

Tuck your pants into your socks and find an opponent to play 1-on-1 hoops under the lights of Wicker Park. Wicker Park is the name of both a small triangular park and the neighborhood that surrounds it, just a couple miles northwest of Downtown Chicago. Beyond the small park, you’ll find quaint shops, restaurants, and some spectacular houses nestled in the nearby streets. A few of our favorites include Dove’s Luncheonette, US #1 Vintage, Arc’teryx, Danny’s Tavern, Asrai Garden, and Saint Alfred.

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Stony Island Arts Bank

It’s worth a slight hike down to Hyde Park to experience Stony Island Arts Bank — a hybrid art gallery, library, and community center. Part of artist Theaster Gates’ Rebuild Foundation, you’ll find rare exhibitions ranging from Frankie Knuckles’ record collection to a portrait of President Obama from every day he served in office. There’s even a small bar on the first floor where local DJs gather on Sundays and take turns spinning records on a big sound system. Check the Bank’s calendar to see what’s happening while you’re in town.

Pro-Tip: Stop by a Frank Lloyd Wright architectural staple, the Frederick C. Robie House, on your way. The Plein Air Cafe next door serves top-notch food and drink as well.

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Source: Rebuild Foundation

Garfield Park Conservatory

Chicago will test your cold weather tolerance and layering skills. Garfield Park Conservatory is a nice place to walk around for an hour and enjoy a little extra fresh oxygen. Walk for free (or donate a few bucks) in a glass ceiling house through two acres of tropical plants. Its Fern Room is a personal favorite oasis in the city. Garfield Park Conservatory will almost always be crowded, but it’s worth it if you just can’t stand the cold outside. Take the Green Line from downtown to the conservatory in 20 minutes or less. Up north? Visit its sister conservatory at Lincoln Park instead.

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Did we miss any of your favorite spots in Chicago? Let us know where you love to get Recreational below.

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