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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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.
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
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
Enjoy a freshly renovated three-level Lincoln Park home in Chicago with a private rooftop deck. This luxurious Airbnb in Lincoln Park, Chicago, offers an open floor plan with a spacious living area and a custom chef’s kitchen with stainless steel appliances, a dining room table for six, and a kitchen bar for three. The home features two main-floor bedrooms with king-size beds and easy access to a fully stocked bathroom. It also includes two half-baths (one on the top floor and one in the basement). The location is safe and convenient, close to the lake, entertainment, retail, and restaurants.
Seven guests, three bedrooms
Price: $335 per night
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.
This modern Chicago Airbnb 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.
With two bedrooms and a dedicated workspace in addition to the spacious living room, this Airbnb in Chicago’s 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.
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.
Check out this sophisticated one-bedroom Airbnb in Downtown Chicago 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.
This Airbnb near Grant Park Chicago 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
This contemporary one-bedroom Airbnb in Hyde Park, Chicago, offers comfort and convenience for city tours or business trips. It features a spacious living area with modern furnishings, hardwood flooring, and a fully furnished kitchen with a granite countertop with all the necessary appliances and utensils for home-cooked meals. The apartment is in a pleasant neighborhood close to restaurants and shops, like the University of Chicago, local shops, restaurants, and attractions like the Museum of Science and Industry and the Obama Presidential Center, making it an ideal place to stay while exploring the city.
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.
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.
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.
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.