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.
Traveling to Chicago? Check out Matador’s Chicago accommodations guides:
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.
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
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
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.
This delightful Chicago Airbnb in Streeterville is conveniently located for public transport, restaurants, theaters, and cultural attractions. Note the chalkboard in the lounge for handy navigation and finding your way around the local area! All rooms are generously proportioned and the kitchen can’t be faulted. There’s a bar on the second floor of the building which is worth swinging by for a brew although light sleepers may appreciate earplugs for weekend stays.
This four-bedroom home in the West Loop is one of the best rentals for families in Chicago. The kids will get their own bedrooms and there’s a fabulous kitchen for throwing together a hearty breakfast. There’s a private patio plus one secure parking space in the garage. For getting around downtown, you can streamline the experience (and avoid parking woes) by hopping on the subway right outside the house.
Dive headfirst into Chicago’s cultural and entertainment hotspots at this one-bedroom apartment rental in The Loop – starting with this property’s communal swimming pool! The space is configured for a couple with the functionality to sleep a further four guests in the lounge. The quartz-topped kitchen has stainless steel appliances while the squeaky-clean bathroom has a rainfall shower and a tub. It’s nigh impossible to find a single flaw at this Guest Favorite Airbnb.
This two-bedroom, two-bathroom vacation rental provides the convenience of a downtown location yet the peacefulness of the suburbs. The unusual layout is part of the house’s charm and makes it easier for couples and families with older kids to establish their own space. Best of all, the unit has a private rooftop deck with skyline views. There’s free parking within the gated complex and the Field Museum is within walking distance.
Situated on the boundary between the Chicago Loop and South Loop, this top-rated vacation apartment gives you the best of downtown and suburban life. The principal bedroom and balcony have spectacular views over the downtown zone which pop after dark. There’s a host of luxury amenities in the building including an indoor pool, rooftop hot tub, basketball court, and gym. It’s a fine option for a weekend away or a longer stay in the Windy City.
This minimalist apartment benefits from sky-high ceilings and wall-to-wall windows to create a sense of a larger space. The balcony is in a prime spot for people-watching over morning coffee as commuters go about their day below and noise isn’t an issue in this part of River North. Each bedroom has a private bathroom and there’s ample storage to cover a longer stay (or a spontaneous shopping spree).
Art lovers and design buffs may well find their own creative juices flowing while staying at this elegant two-bedroom apartment with views of the Chicago River. The space is stylishly turned out with an island kitchen and a cozy nook for reading or surfing the channels. Guests are welcome to use the shared rooftop, seasonal hot tub, gym, and art studio.
Step into this serene apartment where a soft color scheme and warm furnishings invite you to feel at home. The open-plan living room and kitchen are made cozier by the modular couch and small island bar. One bedroom has a king-size bed whereas the other is a queen, each made up with plush bedding for a restful sleep. The location is off the charts; you’ll be able to walk to Michigan Avenue, The Bean, and any theater on your list.
Four guests, guests bedrooms Price: $816 per night
This handsome rental unit has a vintage flair and offers a high level of comfort. It’s curated more like a hotel room with cooking amenities restricted to a Nespresso machine and a microwave. Considering that the city’s best restaurants are right on the doorstep, that shouldn’t be a concern for food-motivated guests. Paid parking is available next door and it’s wise to reserve a space in advance.
Two guests, one bedroom (studio) Price: $371 per night
This Guest Favorite Airbnb in Chicago’s most multicultural district features two lavish bedrooms and a large living room kitted out with mid-century modern furniture and art galore. The fully-equipped kitchen comes with a gigantic fridge and an island where the group can congregate over coffee. Choose Pilsen if you’re looking to experience a different side to the city to the typical downtown offering.
