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Eclectic Pilsen Airbnb
Photograph: Courtesy Airbnb/the host

10 unique Airbnbs you can rent in Chicago

From beautifully refurbished historic homes to posh artist lofts, these eclectic Airbnbs offer one-of-a-kind stays.

Emma Krupp
Written by
Emma Krupp
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No matter how much you love your home, we all need a break from everyday life once in a while. And while you could always hop in your car for a weekend getaway from Chicago, it's worth considering that you can find a radically different change of scenery just outside your neighborhood. From immaculately decorated vintage condos to a full-on treehouse for adults (seriously), the Chicago area offers tons of staycation options that are unlike anything you'll experience in day-to-day living. Get out there, find new things to do in Chicago and live like a tourist in your own city with the help of these wonderfully unique Airbnbs. 

RECOMMENDED: Lakefront Airbnbs to rent for a summer getaway from Chicago

Unique Airbnbs in Chicago

Scratch your itch for luxury with a stay at this huge Prairie-style home, which comes outfitted with a sauna, massage room, heated bathroom floors and a fireplace alongside gorgeous historic architectural touches. Avid readers will appreciate the home's sunlit, stencilled reading room, though the front porch—equipped with rocking chairs—also makes for an appealing spot to curl up with a book.

You'll feel like a veritable bohemian in this sprawling loft, which was built in a converted warehouse space. Exposed piping, brick walls and sky-high wood ceilings evoke echoes of the building's industrial past, but cushy details like a rain shower, stainless steel soaking tub and professional-grade kitchen upgrade the digs to truly luxe status.

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Who said treehouses are just for kids? Head to Schaumburg, a suburb located about 30 miles outside of Chicago, to climb up into this tricked-out cedar treehouse, which sits perched above a koi-filled pond and waterfall. Inside you'll find amenities like a full-sized bed, kitchenette and hi-def TV. Per Airbnb rules, you'll also have access to a room inside the main home in addition the hot tub and gas grill below. 

This Little Village apartment, a recently refurbished unit in a building that dates back to the 1880s, is loaded with tons of vintage charm, from its massive windows to decorative crown moulding overhead. Relax in the elegantly decorated front room or head out into the neighborhood to pick up paletas, which you can savor on the building's shared front porch. 

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Filled to the brim with paintings and sculptures from artists around the country, this River West spot feels more like a contemporary art museum than an apartment. Play the art critic and wander its rooms to appreciate the full scope of work; once you've finished, step onto the balcony for soaring city views. 

Whether you're a labor history buff or not, this 1880s-era workers flat in Pullman—the Chicago neighborhood that was once home to the country's most famous company town—is sure to leave you charmed. Located above a working art studio, this apartment is replete with art and antique touches, but you'd be remiss not to head out into the neighborhood on Airbnb's Labor Tour, which covers the highlights of the area's history.

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River North’s Rock ‘n’ Roll
Photograph: Courtesy Dean Zelinsky

River North’s Rock ‘n’ Roll

Once upon a time, River North was home to Rock 'N' Roll McDonald's, a flagship location tricked out with themed decor and an entire exhibit dedicated to the history of rock and roll. The McDonald's sadly lost its theme in 2017, but you can still relish rock 'n' roll kitsch at this nearby apartment, which is loaded with guitars, Elvis cutouts and old records.

Transport yourself to what looks like the setting for a Southern Gothic novel when you book a weekend getaway at this Victorian-era home, which features 4,000 square feet of parlor rooms and opulent decor. Styled with a New Orleans-esque flair, the home comes complete with high-backed velvet chairs, oil paintings and a fleur-de-lis tiled sunroom—buy yourself a packet of chicory coffee for your stay to complete the effect.

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You'll have tons of room to spread out in this giant, six-bedroom contemporary home located in the heart of Lincoln Park. Hang out by the fireplace on the patio or head down to the lot's private sports court for a game of basketball; if you'd prefer to get your exercise inside, you can check out the gym area stocked with a sauna, weights, a treadmill and a Peloton bike. 

This Pilsen Airbnb, designed and furnished by a pair of artists, is what you wish your aparment looked like. Airy touches, like fiddle leaf fig plants and white wooden floors, are offset by rustic cowskin rugs and a chocolate-colored Chesterfield sofa, while a rain shower head offers a luxurious touch to the bathroom. Cozy up in the art-filled living room for a night of Netflix or head out into Pilsen on foot to explore the neighborhood's famous murals. 

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