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Airbnb Castle
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Amazing Airbnb Chicago homes you can rent

Insta-perfect apartments or historic OTT mansions, Chicago’s Airbnb options offer truly unique alternatives to the city’s hotels. Here’s a few of our favourites

By Stephanie Bernstein and Kris Vire
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In cities across the globe you’ll find quirky, one-off places to stay thanks to Airbnb. But Chicago, more than most, is really on the money when it comes to genuinely individual properties. Where else, for example, could you hope to stay in a Gold Coast mansion designed and built by the leading architects of Modernism? Let alone the iconic former home of an eccentric stone sculpture collector. Chicago has both, and a few more low-key options thrown in for good measure. And, rest assured, you’ll find properties dotted throughout the city, from the tourist hotspots to favourite local hangouts. Whether you’re here for the weekend or planning a longer staycation, there’s sure to be something that’s perfect for you.

RECOMMENDED: Our guide to weekend getaways from Chicago

 

Best Airbnb Chicago Rentals

Photograph: courtesy Airbnb

Avondale escape

Do city living right with a stay in this super sleek loft-conversion, replete with exposed brickwork and modernist furniture design. Make the most of good weather with a leisurely breakfast out on the rooftop desk or, if the temperature has dropped, eat the first meal of the day at the attractive wooden breakfast bar. Located on the border of Avondale and Irving Park, visitors can take advantage of the free garage parking space before jumping on the Kennedy Expressway to downtown or O’Hare.

Castle on Berwyn
Castle on Berwyn
Courtesy Airbnb

Extra, extra!

Part 18th century museum, part lavishly decorated home. The Castle on Berwyn is one of Andersonville’s most famous properties - and rightly so. From the brightly coloured walls to the huge array of antiques on display, there’s so much to look at inside the property you might be tempted to stay home your entire visit. But don’t: this local landmark is only a 20 minute drive from downtown, making it ideally situated for visitors to go out and explore the city. 

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Airbnb Florsheim
Airbnb Florsheim
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Historic hideaway

Rent a piece of history in the Gold Coast when you book the famous Florsheim Mansion for the Arts, which sleeps 12 people in its five well-appointed bedrooms. Given the nature of the space, a hefty security deposit is required up front, but there are plenty of perks that make it worthwhile: You'll rest your head where a shoe heiress once slept, relax near a koi and turtle pond and, of course, be able to say you stayed in the Florsheim Mansion

Wrigleyville Airbnb
Wrigleyville Airbnb
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Kid-approved kingdom

When it's not being rented on Airbnb, this Wrigleyville coach house is home to four kids—and the playful decor and toy supply prove it. Rent the entire rustic four-bedroom pad for the weekend and enjoy recent renovations, including a playspace for kids that's only accessible by ladder. Equipped with a crib, tons of toys and an expansive library filled with bedtime reads, it's no wonder this rental boasts a great rating. 

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Airbnb Oasis
Airbnb Oasis
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Sunny stunner

Appropriately dubbed the "Outdoor Oasis," this home's 1,000-square-foot deck and patio overshadow any of its indoor amenities (and those are pretty spectacular, too). Save this rental for summer months, when you can put the cabana and bar space to good use with an outdoor celebration. 

Airbnb Apartment
Airbnb Apartment
Courtesy Airbnb

Instagram IRL

Hello, gorgeous! This light-filled minimalistic apartment features polished wood floors, indoor plants and all-white decor. The back door opens to a lush yard with a hammock, firepit and grill. And since it's located in the heart of Pilsen, concerts, restaurants and art galleries await just blocks away. 

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Photograph: courtesy Airbnb

South Loop luxury

This high-ceilinged two-bedroom condo sleeps up to six guests. The South Loop high-rise location offers easy access to Columbia College, the Museum Campus and Grant Park—and with laundry in-unit, it might be the ideal perch for an inevitably muddy Lollapalooza weekend.

Hipster Airbnb
Hipster Airbnb
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Hipster paradise

Situated between Wicker Park and Ukrainian Village, this gorgeous home is made for artists looking for a healing hiatus. Make the vintage art your muse and detox in the underground in-home sauna at this photographer-owned abode. Bonus points: The well-equipped kitchen is the perfect location for a relaxing night in or post-dinner drinking.

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Airbnb Modern
Airbnb Modern
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Artsy abode

If you spend your free time visiting galleries, you'll love this century-old Chicago greystone owned by an artist and Airbnb award recipient. Situated in the heart of Uptown's entertainment district, the space is filled with contemporary art, complex interior design and other curated works. Stay here and you can skip the Art Institute to browse the bedroom decor.

Chicago loft
Chicago loft
Photo: courtesy Airbnb

Playful loft

Sleeping up to eight guests, this loft in River West makes for the perfect party pad during your visit to Chicago. Within its vast, but warmly decorated industrial walls, lies a cinema room, jacuzzi and a pool table, as well as the usual amenities, like wifi, washer/dryer and bathroom bits. With all that at hand, you'd be tempted to stay in, but venturing out even a few minutes' walk will lead you to Wicker Park, Bucktown and a welath of shops, cafes, bars and restaurants.

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Photograph: courtesy Airbnb

Rock out in River North

Indulge your inner rock star at this rococo River North music lover’s abode. Decked out in rock & roll memorabilia and featuring an antique hi-fi to play your own tunes, this two-bedroom apartment features other fun touches like a carved wooden canopy bed. Proximity to the CTA Brown and Red lines makes getting anywhere a breeze.

Airbnb Bachelor Pad
Airbnb Bachelor Pad
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Bachelor(ette) pad

Celebrating a special bride or groom with a group trip to Chicago? Stay in this massive Uptown mansion decked out with hardwood floors, eight bedrooms, three living rooms and plenty of parking spots. With three and a half bathrooms, everyone will have space to get ready, and the kitchen is perfect for a pregame.

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Cubs Airbnb
Cubs Airbnb
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Cubs confine

If you loved the Cubs before everyone bandwagoned in 2016, this Airbnb is for you. Ideal for a sports-filled weekend away, the two-bedroom condo in the heart of Wrigleyville is decked out in crazy Cubbies memorabilia. Seriously—the space features autographed equipment and actual stadium seats. The host's only request: keep your hot dogs and beer cans far away from the white leather sofa.

Airbnb
Airbnb
Courtesy Airbnb

Relaxation overload

Treat yourself to this gorgeous Uptown home equipped with a spacious sauna and soaker tub, heated floors, a beautiful kitchen, three bedrooms and plenty of added amenities. The house is located within walking distance of restaurants, bars and shopping, making it easy to venture out for anything you may have forgotten.

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Airbnb Chicago penthouse
Airbnb Chicago penthouse
Photo: courtesy Airbnb

Modern oasis

Live like a high-flyer for a weekend or longer with a stay in this uber modern and ultra luxurious penthouse suite. Located in the Loop, you get jawdropping views of both the city skyline and Lake Michigan – completely unhindered views through floor-to-ceiling windows, might we add, which run around the entire apartment. You can sleep up to ten people here, and enjoy free use of the building's pool, gym and rooftop deck.

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