Best Airbnb Chicago Rentals
This beautifully appointed studio loft near the border of Avondale and Irving Park features tons of exposed brick, a modern kitchen and a rooftop patio space. If you’re driving in the city, this rental conveniently offers free parking and easy access to O’Hare or downtown via the Kennedy Expressway.
Calling all fairytale fanatics. The Castle on Berwyn, one of Andersonville's most famous properties, is filled with enough ornate art and antiques to make you feel like total royalty. Architectural buffs will appreciate the fact that massive carved stones from old, demolished Chicago buildings dot the backyard garden and patio. Don't be surprised if a historic home tour passes by during your stay.
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.
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.
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.
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.
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 makes the perfect backdrop 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.
If you're looking for something totally different, this East Pilsen space should do the trick. Owned by a local photographer, the apartment sleeps two to eight with a lofted bedroom, indoor hammock and two extra beds, plus a few couches. The projector and pool table are added perks that make staying in a breeze.
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.
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.
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.
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.
This sleek, uber-modern five-bedroom home makes it easy to play house or host a small group for the weekend. If you're not up for putting the kitchen to use, there are dozens of popular bars and restaurants just around the corner. But the hands-down best feature here is the two-story outdoor dining area, where you can grill, lounge around and laze the day away. If it's chilly, light the fire pit or hop in the hot tub to warm up.