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Best Airbnbs in Chicago
Photograph: Airbnb

The best Airbnbs in Chicago

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.

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No matter where you are in the world, Airbnb is always teeming with quirky, one-off places that make your trip a little more special and less conventional. And in Chicago that stands more than most. From modernist masterpieces to homes of eccentric stone collectors, there are plenty of fabulous rental options dotted throughout the Windy City, all within commutable distance of the great Chicago sights and attractions

Whether you’re here for the weekend or planning a lengthier staycation, Chicago is bound to have an Airbnb perfect for your trip. Read on for our lowdown on the city’s finest Airbnb rentals. 

RECOMMENDED: Our guide to weekend getaways from Chicago 
RECOMMENDED: The best hotels in Chicago

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Best Airbnb Chicago Rentals

The loft escape in Avondale
Photograph: courtesy Airbnb

1. The loft escape in Avondale

Do city-living right with a stay in this super sleek loft-conversion, replete with exposed brickwork and modernist furniture design. Truly aesthetic ways of blending urban cool with indoor comfort. Make the most of good weather with a leisurely breakfast out on the rooftop desk or, if the temperature has dropped (this is Chicago, people) eat the first meal of the day at the attractive wooden breakfast bar. Either way, a top start to the day. 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. Great times all round. 

The luxury mansion near Gold Coast
Supplied by Airbnb

2. The luxury mansion near Gold Coast

This is the mansion of dreams. This amazing, historic, single-family home in Chicago's Gold Coast sleeps 12 guests. Nice. Given the size of the house, it doesn't come cheap and will set you back quite a lot, but once you split it between your 12 guests, it's a lot more doable. And there are plenty of perks that make it worthwhile: There are three huge ornate gas fireplaces you can use for those cosy winter days, you'll have access to a gourmet chef's kitchen with Wolf range and sub-zero refrigerator – and you'd be walking distance to almost all downtown Chicago attractions. Sounds like heaven to us.

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The peculiar flat in Wrigleyville
Courtesy: Airbnb

3. The peculiar flat in Wrigleyville

Peculiar but posh; doesn't sound like much of a compliment, does it? But it certainly is. This Airbnb in Wrigleyville, Chicago is quirky, inviting, and has a touch of vintage charisma. It's the perfect place for a relaxing stay, thanks to the secluded vibe of the area, but still super close to shops and restaurants. Sleeping two guests in a cozy king-sized bed, you can fall in love all over again with a romantic trip for two, or have a bit of a self-care staycation after the stresses of normal life. Fab for remote working (if you can't resist a work email) and has, almost, a whole library of books. Sounds like heaven. 

The artsy abode in Uptown Square
Courtesy Airbnb

4. The artsy abode in Uptown Square

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, if you want. Or do both, your holiday innit, one thing's for sure though, you won't be lacking for good views. That aside, this is a properly kept and tastefully styled place to spend a few nights. 

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The opulent luxury home in Old Town Triangle
Supplied by Airbnb

5. The opulent luxury home in Old Town Triangle

Situated in the heart of Historic Old town triangle, this gorgeous home is made for vacantioners who are looking for luxury and opulence. Bonus points: You'll be situated on a quiet, tree-lined and secluded street, but still in close proximity to great restaurants, shops, Lincoln park Zoo, Lake Michigan,Brown line and more. Oh, and the bathrooms are maybe the real standouts. They feature Carrera marble throughout, towel warmers and heated floors. And, the master bathroom has a soaking tub and multi-head body sprays.

Celebrating a special bride or groom with a group trip to Chicago? Stay in this massive restored 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, plus there’s plenty of lounge space to chill out and wind down and the kitchen is perfect for a pregame.

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The rock out in River North
Photograph: courtesy Airbnb

7. The 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. You'd imagine someone like Courtney Love or Axl Rose to call this place home, with the luxury-rock vibes throughout. You're also right next to the Loop here too, so it isn't just whistles and bells inside. Free parking too, should it be needed! 

The high-spec loft in Lake View
Courtesy Airbnb

8. The high-spec loft in Lake View

First things first: the owners of this ace Chicago Airbnb give $5 from each rental to a local children’s charity. Nice huh? An incentive to stay here alone. But, 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. You're also 1/2 mile to the Brown & Red Line trains, less than a mile to Wrigley Field, and 1.5 miles to the lakefront. Blissful. 

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The stunning condo in East Village
Courtesy Airbnb

9. The stunning condo in East Village

Sure, the East Village location (between Wicker Park and West Town) is a cracker when it comes to restaurants, culture, bars, and more, 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. Ridiculous. Hotel who? Live it like a large home-owner this trip.

The Cubs confine in Wrigleyville
Courtesy Airbnb

10. The Cubs confine in Wrigleyville

If you loved the Cubs before the bandwagon (we put that at about 2016 or so), 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.

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The architectural treasure near Jarvis Beach
Photograph: Airbnb

11. The architectural treasure near Jarvis Beach

Look, we know when we say that someone’s an architectural legend, that probably sounds like the kind of thing that flies over a whole load of heads. But superstar architects didn’t get much more famous than Frank Lloyd Wright – and Chicago’s full of his wondrous creations. Here’s another of those, a place called the Emil Bach House that is about a block west of Jarvis Beach and features all of FLW’s signature sharp edges, innovative airiness and wooden finishes. It’s a proper design treasure.

The old spring factory in East Village
Photograph: Airbnb

12. The old spring factory in East Village

This rental’s sure to put a spring in your step – and not just because it’s in an old spring factory. Boasting a pro-level kitchen, an unbeatable collection of rare teas, a Japanese stainless steel soak tub and endless knick-knacks themed around the building’s industrial past, it’s safe to say there aren’t many (if any) rentals in Chicago quite like this one.  

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