Chicago is one of the world’s great cities and there are countless reasons why you should visit this Toddlin’ Town. The Windy City will keep you entertained from the infamous Lollapalooza to the delicious cuisines, cool hiking trails and unique museums, you surely will not get bored. While boutique hotels are certainly one way to go when it comes to accommodation, Airbnbs are often cheaper — or so incredibly unique that they’re worth the splurge. Whether you’re looking for a prime location, rockstar digs, great value, or something totally off beat, you’ll find it on our list of the coolest Airbnbs in Chicago.
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We hope you love these Airbnb Chicago vacation rentals! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
1. Chicago home designed by Frank Lloyd Wright
Airbnb is loaded with properties that are so effervescent they might make you reconsider your plans to “get out and explore the city.” None so much as a home designed by Frank Lloyd Wright himself. The Emil Bach House, as this legendary pad is known, was built in 1915 using Prairie materials. It’s nickname is “stacked cubes” and it’s easy to see why — right-angle contours and a design way ahead of its time make this Chicago’s best Airbnb, and one of the few FLW homes you can actually stay in.
Six guests, three bedrooms
Price: $386 per night
2. Nine-bedroom Airbnb in Uptown Chicago
Uptown is a neighborhood with strong links to its past, including the iconic Green Mill jazz club and ballroom-turned-concert-venues The Aragon and The Riviera. This brownstone mansion connects back to a bygone era in exactly the same way while stylish amenities keep the home full of modern comforts. Being located at the southern edge of Uptown, the property is also very close to the Wrigleyville neighborhood but still somewhat removed from the busyness of that area.
Sixteen guests, nine bedrooms
Price: $750 per night
3. Eclectic loft Airbnb in River West
It’s hard to beat River West if you want a hip location, and this eclectic loft in an old factory is an especially great place to stay. The open floor plan, hardwood floors, exposed brick, 20-foot ceilings, and gorgeous interior design create a space that is as homelike as it is hip. With an in-unit movie screening room with surround sound, you might not want to leave. But if you do, the surrounding neighborhood and nearby Old Town are full of great bars, restaurants, and the legendary Second City comedy club.
Eight guests, three bedrooms
Price: $390 per night
4. Greystone Airbnb in Wrigleyville
This brand new designer home in a historic Greystone is an ideal place for a group of friends in town for a Cubs game, for a bachelor or bachelorette trip, or even a large family. The stylish home looks like it was designed for a single guy, but its simple style will work for anyone. The home can take up to 10 guests in five bedrooms and is located right near Wrigley Field and the hundreds of bars and restaurants that dot the neighborhood.
Ten guests, five bedrooms
Price: $400 per night
5. Light-filled loft Airbnb near West Town
Connect to Chicago’s industrial past in this converted loft in an old building while enjoying modern style and convenience. This beautifully appointed home is ideal for a couple or small family and has a perfect location between Wicker Park and River North along the Blue Line train and Kennedy Expressway, which both run between downtown and O’Hare Airport. It’s also near many popular West Town attractions like the WNDR Musuem.
Four guests, one bedroom
Price: $111 per night
6. Luxury apartment Airbnb in Lakeview
This modern loft in Lakeview has industrial-chic design practically oozing out of the exposed brick walls and across the hardwood floors. The two-bedroom, two-full-bathroom space is perfect for two couples coming into town for a weekend concert or baseball game. The loft is steps away from the Belmont Brown, Red, and Purple Line train stops. Wrigley Field is just a 10-minute walk away, and the neighborhood is full of great cafes, restaurants, bars, and clubs. The neighborhoods of Wrigleyville, Lincoln Park, Boystown, and the lakefront are all within a mile.
Four guests, two bedrooms
Price: $129 per night
7. Spacious loft Airbnb in Lakeview
With two bedrooms and a dedicated workspace in addition to the spacious living room, this loft in Lakeview is everything you need to settle in for a few days or a few weeks in the Windy City. The kitchen is open and modern, with all the tools you need to prepare restaurant-quality meals, though the surrounding Lakeview neighborhood also has you covered on that front. The unit is right by the Brown Line for easy access to the entire city, and within walking distance of nightlife, dining, and shops.
Four guests, two bedrooms
Price: $159 per night
8. Unique Lincoln Park Airbnb
The Lincoln Park Zoo is one of Chicago’s main attractions, and you’ll be blocks away in this cute, modern duplex. The lakefront is an easy stroll away, meaning you can fit in a day’s worth of entertainment, shopping, dining, and exercise in one go while simultaneously ticking off the box of things to see in Chicago. Oh, and the apartment itself is charming to the point that a lazy morning brunch or happy hour cocktail while gazing out the large windows won’t sound bad, either.
Two guests, one bedroom
Price: $125 per night
9. Downtown Chicago Airbnb with stunning views
Check out this sophisticated one-bedroom apartment right in the south loop. This apartment features a spacious living room with floor-to-ceiling windows showcasing the Chicago skyline, a fully equipped kitchen area, a balcony, and a cozy bedroom. Get out and explore the windy city, as the apartment is near many attractions like Victory Tap, M Lounge, and Little Branch.
Four guests, one bedroom
Price: $157 per night
10. Penthouse Airbnb near Grant Park
This penthouse is perfect for your stay. Gather your friends and make this home base for your Chicago stay. This seven-bedroom penthouse features a cozy living room, a well-equipped kitchen, and seven bedrooms. There is a shared rooftop, gym, and kitchen area. Enjoy the scenic skyline, park, lake, harbor, and marina views.
Seven guests, three bedrooms
Price: $248 per night
11. Chic Airbnb near Hyde Park attractions
Stay at this Hyde Park Chicago three-bedroom apartment on your Chicago getaway. This modern apartment has a cozy and spacious living room, kitchen, and dining area, among other amenities needed for your stay. Nestled right in the heart of Hyde Park, this apartment is near many popular attractions.
Six guests, three bedrooms
Price: $57 per night
12. Contemporary Hyde Park Airbnb
Located on the third floor of a multi-residential building is this stylish apartment. This four-bedroom apartment has a large living area, a fully equipped kitchen, and four bedrooms with two full bathrooms. Get out and explore the town, as downtown is only 15 minutes away, or visit the University of Chicago campus next door.
Seven guests, four bedrooms
Price: $110 per night
13. Rock-n-Roll themed Airbnb
Immerse yourself in this unique Airbnb Chicago apartment. This rock-n-roll-themed apartment is decorated with tons of rock-n-rock memorabilia and has a spacious living room, a fully equipped kitchen, two bedrooms, and two full bathrooms. This apartment is located above a trendy restaurant and is only a few minutes from Mag Mile and the Loop.
Six guests, two bedrooms
Price: $322 per night
14. Stylish quiet Airbnb with private outdoor space
This quiet home is the perfect stay while in Chicago. This renovated home is decorated with grayscale walls, rustic accents, and unique wall art throughout the house. The home has a spacious, cozy living room, a full kitchen, and a private outdoor space. Sit back and relax as the home is in a quiet neighborhood but enjoy all that Chicago has to offer by visiting restaurants, shops, and bars ½ block away.
Six guests, two bedrooms
Price: $187 per night
15. Spacious Loft Airbnb in the heart of Wicker Park
Situated right in the heart of Wicker Park is this spacious loft. This cool loft has an open floor plan with the living, kitchen, dining area, and French doors separating the bedroom. The loft is right in the middle and near many restaurants, cafes, shopping, and more. 
Four guests, one bedroom
Price: $202 per night
A version of this article was previously published on October 3, 2018, and was updated on April 8, 2021, with more information.