The Best Airbnbs in Chicago, From Frank Lloyd Wright-Built Homes to Modern Lofts
If you’re interested in exploring the breadth and depth of Chicago’s renowned architecture, there’s a good chance you can start in your Airbnb. For a city that’s known the world over for its eclectic collection of modernist meets gothic meets neoclassical, many examples of the Windy City’s historic cityscape lie outside the downtown corridor. From industrial lofts with soaring ceilings in the West Loop to a restored prairie-style home built by Frank Lylod Wright or bright and airy condos in Oak Park, these Airbnbs offer a taste of what makes this city so spectacular. Use them as your home base for some of the city’s best activities: an architecture boat tour along the Chicago river, a bustling food and bar scene, and an inspired art scene, plus the must-visit beaches along Lake Michigan.
While we have not stayed in every Airbnb featured, unless otherwise stated, these listings are vetted based on Superhost status, amenities, location, previous guest reviews, and decor.
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- Courtesy Airbnb
Gallery-meets-condo in River West
The vibe: Forward-looking, with one-of-a-kind pieces by emerging artists
Bed & bath: 3 bedrooms, 2 baths
Top amenities: An incredible art collection sourced by the owners and a brightly painted mural covering an entire wall
Nearby attractions: The Chicago Sky Deck, Chicago Theatre, Millennium ParkPart home, part functioning art gallery, this one-of-a-kind unit features artwork from the country’s emerging contemporary artists. Like a traditional gallery, some art pieces will shift as new work becomes available, meaning no stay is ever quite the same. Along with paintings, sculptures, and a floor-to-ceiling mural, you’ll also find more interactive art, including painted blinds and a playful piece on the functioning fireplace. The bedrooms and bathrooms boast a more Scandinavian design, with bright-white sheets, muted towels, and verdant plants. The neighborhood—River West—is just as energetic, with unique shops, restaurants, and attractions.
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Magnificent Mile Masterpiece
The vibe: An upgraded apartment with sweeping lake views
Bed & bath: 2 bedrooms, 2 baths
Top amenities: Open floor plan, upgraded appliances, rooftop with sweeping views of the lake, and direct access to famed Michigan Avenue
Nearby attractions: Michigan Ave staples like the Chicago Athletic Association, the American Girl Doll store, Millennium Park, and the BeanA juxtaposition among the tall, modern high rises of Chicago, this quaint and boutique condo on the Magnificent Mile is a rare find. With views of the downtown cityscape, Lake Michigan, and the bustling sidewalks of the Mag Mile, the location is the star of the show with this unit. However, if you can step away from the views, you’ll find a warm and inviting interior welcoming you in. Boasting an open floor pan, contemporary furniture, and updated bathrooms , you’ll feel right at home. The real highlight is the upgraded masterful rooftop with a large-screen TV, ample seating, and a grill. Of course, you won’t need the TV once you see the show-stopping view of the lake.
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Colorful oasis
The vibe: Tropical
Bed & bath: 3 bedrooms, 4 baths
Top amenities: A tropical-inspired interior that’ll transport you the beach, bright furnishings and funky decor, and room for up to 14 guests
Nearby attractions: Emporium bar and arcade, Mott Street (known for their burgers), and the bi-level Subterranean music venueOne step into this brightly painted condo, and you’ll feel like you’ve been transported to Miami. With brightly painted walls, neon signs, and a mix of modern and 70’s-inspired art, this is a haven for those seeking more color. The vibe carries itself throughout the space, including the bathroom, which boasts a larger-than-life sinking tub painted electric blue (and comes equipped with an inflatable flamingo). As eye-catching as the interior is, the highlight is the patio, which will comfortably seat up to six people. Don’t worry; the tropical theme carries out here, too, with bright furnishings and living palm trees.
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Modernist loft in Pilsen
The vibe: Bright, bold, contemporary
Bed & bath: 2 bedrooms, 1 bath
Top amenities: A bright yellow wall flanking the kitchen, airy rooms with modern decor, two miles from downtown South Loop
Nearby attractions: 16th-Street murals painted by revered Chicago artists, the Tahlia Hall concert venue, and Pilsen Yards—a Mexican-inspired eatery, bar, and music venueThose with a taste for modern decor will feel right at home in this bright loft in Pilsen. Enjoy your coffee in the yellow sunroom, read a book in the cozy loft bed, or pen your debut novel in the sun-drenched office nook. The main bedroom is right off the large renovated kitchen, featuring a retro pink-painted bathroom with a tub. The location in Pilsen, a south side neighborhood that is rich in Latino heritage and home to the Mexican Art Museum, positions you for a cultural visit. Known as the Chicago Arts District, the area’s buildings are covered in murals and mosaics. Make time to indulge in the local cuisine, including noshing on authentic tacos.
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Restored factory in Wicker Park
The vibe: A 1900s refurbished factory in trendy Wicker Park
Bed & bath: 1 bedroom, 2 baths
Top amenities: 14-foot ceilings with exposed brick walls and a large Japanese-style soaking tub
Nearby attractions: Violet Hour—one of Chicago’s hippest bars, the 606 walking and biking trail, the Robey HotelThis restored one-bedroom loft is in a converted tea factory in hip Wicker Park. Thanks to the owner’s eye for detail and appreciation of Japanese culture, you’ll find little nods to Japan throughout—from the soaking tub in the master bath to the bamboo wall behind the bed. Industrial light fixtures, exposed brick and pipes, and a window-panel wall pay homage to the building’s history. If you can pry yourself away from the professional grade kitchen, head outside and explore the hood’s hip restaurants and bars, including local faves Etta and Delta.
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Spacious home in Wicker Park
The vibe: A lavish five-bedroom for discerning travelers
Bed & bath: 5 bedrooms, 3.5 baths
Top amenities: 75-inch TV, a large patio with city views, luxurious gold and marble accents
Nearby attractions: The retro Wormhole coffee bar, the Damen Blue Line train station to zip to neighboring Logan Square or downtown, the 606 walking trailA perfect blend of vintage meets modern luxury, this opulent five-bedroom mansion in Wicker Park has everything you need to feel at home. Unwind in the entertainment room with a 75-inch TV and popcorn machine, enjoy a cocktail al fresco on the patio or play chess next to the gold fireplace. If you can peel yourself away from the endless amenities, head out and enjoy everything Wicker Park has to offer, from the 606 walking path connecting to other neighborhoods of the city, to the amazing restaurants and nightlife.
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Hip guest house in Humboldt Park
The vibe: Bright and airy home perfect for two guests
Bed & bath: Studio, 1 bath
Top amenities: Cozy studio with 14-foot ceilings and open bath concept
Nearby attractions: Humboldt Park Boathouse and pond, National Museum of Puerto Rican Arts and History, Papa’s Cache Sabrosa—one of the area’s most popular restaurantsWith a very unassuming entrance, you’ll be pleasantly surprised when you enter this airy studio in Humboldt Park. What it lacks in size it makes up for in design, with beautiful artwork, plenty of plants, and a renovated bathroom complete with a claw-foot soaking tub. The kitchenette features everything you need to get by, so it's best to take advantage of Humboldt Park and neighboring Wicker Park’s diverse food scene. Spend your days viewing local artists’ murals or paddling through the picturesque lagoon at the Humboldt Park boathouse.
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Sprawling penthouse in Old Town
The vibe: Just a hop and a skip away from renowned Second City
Bed & bath: 5 bedrooms, 4 baths
Top amenities: 4,000-square-feet with large, floor-to-ceiling windows, roof deck overlooking Willis (Sears) Tower
Nearby attractions: Magnificent Mile on Michigan Ave, Second City comedy club, local favorite North Beach, Lincoln ParkIf you want to explore one of Chicago’s trendiest neighborhoods in style, check out this 4,000-square-foot penthouse in Old Town. Just a few minutes from downtown, Old Town boasts incredible views of the cityscape, amazing restaurants, and the famous Second City comedy club and school. This apartment’s highlights include exposed brick walls and 120-year-old barn doors leading to a private rooftop deck overlooking the city. Plus, you’ll find four bedrooms, four full baths (including a hot tub with the primary room), two kitchens, and two laundry rooms.
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Bright home in Edgewater
The vibe: Steps from the beach and Loyola University
Bed & bath: 4 bedrooms, 2 baths
Top amenities: Just half-a-mile to the beach, sunroom, screened porch
Nearby attractions: Loyola University and neighboring Northwestern University, Montrose Beach, Foster Beach, Lincoln Park and ZooAvailable to rent as both a single floor rental or a massive four-bedroom duplex, this sun-soaked home is a respite from the bustle of the city. A quick ride on the blue line or a 10-minute drive from downtown, Edgewater is home to many of the city’s brightest students and plenty of late-night eateries, thanks to its proximity to Loyola University. The home features floor-to-ceiling windows and French doors that lead to the screened-in porch. There are craftsman details throughout, including wood sconces, original restored floors, and paneled ceilings. A second porch can be found on the duplex’s second floor, featuring hammock swings, ivy walls, and a beautiful view.
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Restored Frank Lloyd Wright home in Rogers Park
The vibe: A Frank Llyod Wright masterpiece
Bed & bath: 3 bedrooms, 2.5 baths
Top amenities: Peaceful Japanese-style rooftop garden
Nearby attractions: Smaller, less-trafficked beaches like Rogers Beach and Leone Beach Park, Loyola University, the Block Museum of Art in EvanstonMeticulously restored, the Emic Bach home—designed by famed local architect Frank Lloyd Wright—is a steal at just over $500 a night. Located in Rogers Park, this home is next to Loyola University, steps from Lake Michigan, and walking distance to plenty of up-and-coming restaurants. The home itself is a work of art, with a beautiful built-in desk, a large living room, and outdoor patios off of each bedroom. The pièce de résistance is the second floor balcony, complete with a Japanese tea house, immaculate gardens, and ample outdoor seating. Built in 1915 for one of Wright’s admirers, this house is a must for art and design-lovers.
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Chic corner loft in Fulton Market
The vibe: Live and eat like a local in one of Chicago’s best food neighborhoods
Bed & bath: 3 bedrooms, 2 baths
Top amenities: 15-foot ceilings with large windows and brick walls
Nearby attractions: Access to some of Chicago’s most popular restaurants, including Oriole—two Michelin Stars, Publican Quality Meats, and bohemian-inspired AbaLocated in one of the city’s best food neighborhoods, you’ll have no trouble finding great places to eat when you’re staying in this 1920’s corner three-bedroom loft in Fulton Market. With 15-foot ceilings, the large windows offer incredible views of the neighborhood, and the rest of the 2,500-square-foot loft features restored concrete floors and exposed brick and timber. You’d be remiss not to try some of the neighborhood's best restaurants, including Girl and the Goat, Roister, and Aba, or to explore the area’s local shops and galleries. Additionally, you’re just a quick Uber ride away from the Magnificent Mile, the riverwalk, and Millennium Park.
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Private penthouse in Ukranian Village
The vibe: A renovated penthouse steps from the cultural epicenter of Ukrainian Village
Bed & bath: 2 bedrooms, 2 baths
Top amenities: Sweeping view of downtown Chicago and a large patio for entertaining
Nearby Attractions: The Delta Gift Shop—which sells hand-made gifts that support the Ukrainian community, the Ukrainian National Museum, Tryzub Ukrainian KitchenYou’d be hard pressed to find a better view of the city than this private penthouse in Ukrainian Village. Featuring a large patio on the roof and a smaller patio off the living room, there are plenty of ways to take in the skyline here. Inside, there are rich leather furnishings and floor-to-ceiling windows sunning the space in natural light, a large kitchen, and two bedrooms and baths. This westside neighborhood is home to over 50,000 Ukrainian families - the second largest population in the country - so be sure to check out the area's many tributes to the home land, including the Ukrainian Institute of Modern Art, the Delta gift shop, and the TryZub Ukrainian kitchen.
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Mid-century townhouse in Wrigleyville
The vibe: Mid-century home with bountiful architectural charm
Bed & bath: 3 bedrooms, 3.5 baths
Top amenities: Fully renovated bathrooms with modern amenities and a cozy patio with plenty of space to sit
Nearby attractions: Wrigley Field, home to the Cubs, the Zachary Hotel, local favorite Big Star tacosJust steps from Wrigley Field, this three-bedroom home in Wrigleyville is the ultimate pad for baseball fans. Decorated with chic mid-century modern furniture, you’ll feel right at home on the cozy tufted couches and in the sleek, updated kitchen. The master bathroom features heated floors, a soaking tub, and a steam shower, and the small outdoor patio is perfect for sipping cocktails or noshing on hors’ devours. The nearby LGBT-friendly Boystown has non-stop nightlife (including discos!) as well as cafes and bistros.
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Trendy condo in Uptown
The vibe: Cozy one-bedroom ideal for a couple or solo traveler
Bed & bath: 1 bedroom, 1 bath
Top amenities: Large windows with a bounty of natural light and a prime location just a few blocks from the beach
Nearby attractions: Quick and convenient to the Red Line (L train line) and Montrose Beach, the Green Mill jazz club—opened in 1907, and 121-acre Graceland CemeterySituated on a quiet, tree-lined street, this one-bedroom condo in Uptown offers a tranquil oasis from the downtown noise. The big windows let in loads of natural light, illuminating the spacious living room, large dining room, and master bedroom. Conveniently located just six minutes from the Wilson red line, you can quickly zip downtown or to other nearby neighborhoods, including Andersonville, Edgewater, and Ravenswood. The highlight of the area is Montrose Beach, which is steps away from the Airbnb and features a waterfront restaurant, dog beach, bird sanctuary, and miles of walking trails along the water. You’ll also find jazz clubs and vintage theaters, thanks to the area’s history as a booming nightlife destination during prohibition.
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Handcrafted gallery in River West
The vibe: A funky artist's lair
Bed & bath: 3 bedrooms, 4 baths
Top amenities: A wide variety of contemporary art
Nearby attractions: Aire Ancient Baths spa; Intuit, the Center for Intuitive and Outside Art; the hipster highway Milwaukee Avenue— which intersects Wicker Park, Logan Square, Noble Square, and DowntownThere’s a reason this River West apartment is called “the gallery.” This three-bedroom condo is part of Open House Contemporary, a collection of homes that feature handpicked artwork from America's emerging artists. Situated in the up and coming River West neighborhood, you won’t find better views of the city anywhere. Soak in the cityscape from the living room’s floor-to-ceiling windows and enjoy the amazing artwork that’s peppered throughout (including the lamps and hand-painted murals). Nearby, you’ll find plenty of restaurants and cafes, plus direct access to the “hipster highway” (Milwaukee Ave) and the 606 walking path.
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Airy condo in Forest Park
The vibe: Tree-lined retreat
Bed & bath: 3 bedrooms, 1 bath
Top amenities: Dedicated workspace, three-season porch
Nearby attractions: Metra, Green Line, shops, bars, restaurantsIf you need a break from the city, stay in this three-bedroom respite in Forest Park. The second-floor condo has a screened-in back porch, a spacious living room, and a large renovated kitchen. The adjacent, tree-lined neighborhood of Oak Park is home to adorable shops, eateries, and Frank Lloyd Wright-designed homes. Plus, the Metra and “L” are within walking distance, so you can shuffle to and from downtown in less than 30 minutes.
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Playful, vintage apartment in Andersonville
The vibe: An eccentric, retro paradise with a big personality
Bed & bath: 2 bedrooms, 1 bath
Top amenities: Direct access to the Swedish-inspired Andersonville neighborhood minutes from the lake
Nearby attractions: The Swedish History Museum, Women and Children First bookshop, and Hopleaf breweryFeaturing yellow walls, turquoise blue accents, and colorful artwork, this two-bedroom condo in the heart of Andersonville will brighten your mood. Modern and minimal, you’ll find a cozy living room, comfortable furnishings, and a beautifully restored kitchen with updated appliances. Outside the condo’s doors is quirky and eccentric Andersonville, a north side neighborhood with Swedish roots. You can walk from home to the antique and boutique shops for a pleasant afternoon activity. The area is also home to and one of the city’s largest LGBTQ+ communities, as well as an amazing food scene that offers everything from small-plates to hearty German fare.
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