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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

Written by
Kris Vire
Stephanie Bernstein

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

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Best Airbnb Chicago Rentals

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.

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


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. 

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.


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.

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.


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.

First things first: the owners of this ace Chicago Airbnb give $5 from each rental to a local children’s charity. Nice huh? They’re every bit as considerate with the fixtures and fittings at this gorgeous loft too, with a high-spec interior kitted out in classic indlustrial-chic style. If you want a tip? Ask the owners where to party – they own a DJ business.


Sure, the East Village location (between Wicker Park and West Town) is a cracker but you might not want to leave this place. Just look at it. There are some high-quality finishes throughout but we’re most stoked about the giant shower and bathtub, and the two private, outdoor decks serving up jaw-dropping views of Chicago. Bliss.

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