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Chicago is one of the world’s great cities, and there are countless reasons why you should visit this Toddlin’ Town. 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.
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.
Price: $386 per night
2. Nine bedroom mansion in historic neighborhood
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.
Price: $750 per night
3. Wonderfully eclectic loft in former River West factory
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.
Price: $390 per night
4. Bachelor pad just steps from Wrigley Field
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.
Price: $400 per night
5. Light-filled loft in perfect location
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.
Price: $111 per night
6. Luxury loft near Wrigley Field
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.
Price: $129 per night
7. Immaculate lakeview penthouse condo
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.
Price: $159 per night
8. Unique Lincoln Park duplex apartment
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.
Price: $125 per night
9. Historic Gold Coast rowhouse with garage parking
If you’ve seen Chicago portrayed in the movies, you’ve seen its historic rowhouses. Nothing defines city living here like the old brick homes stacked next to each other in near perfect symmetry. This classic home even comes with garage parking, a real luxury for anyone living (or staying) in a major city. Located in Chicago’s coolest area, you’ll be able to walk to nightlife, pizza, beer, and the train, and the home itself is modernized with a dedicated workspace and clean decor. Up to 10 guests can share the four bedrooms.
Price: $591 per night
A version of this article was previously published on October 3, 2018, and was updated on April 8, 2021, with more information.
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