The 18 best Airbnbs in Chicago from East Village to Uptown Square

Neighborhood: Fulton Market in the West Loop.

Live it up in one of the most buzzing neighbourhoods in Chicago, in this penthouse apartment so easy on the eye it’s been featured in Architectural Digest. Situated on the top floor of a historic 1920s building overlooking Fulton Market, it’s a huge space with 15-foot-high ceilings, huge windows lining the bare brick walls and vast polished concrete floors. The big open-plan living, kitchen and dining area is perfect for entertaining large groups, while the bedrooms and minimal but stylish with crisp white linen and seven-foot tall windows with views across the city. 

Time Out tip: Walk two minutes over to Randolph Street's famous ’Restaurant Row’ for a cocktail at Lone Wolf or a reservation at Girl & the Goat, then grab late-night tacos at Au Cheval before heading back up to watch the sunset over the neighborhood skyline. And boy oh boy do we have the perfect food guide for you. Check out our guide to the best restaurnts in West Loop.

Sleeps: 12 people.

Perk: Huge windows.

Price: From $440 per night.

Neighborhood: Lincoln Park in the Mid North District.

Nothing says living in the city like exposed brick in every room. This gorgeous duplex apartment in the heart of Lincoln Park, Chicago, is ideal for couples or people on business to the city. Two people can sleep comfortably in the queen-sized bed located on the top floor of the duplex, with a bathroom and closet. The kitchen is fully equipped with everything you might need, and there's space outdoors with seating if you wish to have your morning brew with the birds. 

Time Out tip: It's only a 5-minute stroll to Lincoln Park Zoo, one of the last free-admission zoos in the country.

Sleeps: Two people.

Perk: Private outdoor patio.

Price: From $230 per night.

Neighborhood: Wrigleyville.

Peculiar but posh; doesn't sound like much of a compliment, does it? But it certainly is. This Airbnb in Wrigleyville, Chicago is quirky, inviting, and has a touch of vintage charisma. It's the perfect place for a relaxing stay, thanks to the secluded vibe of the area, but still super close to shops and restaurants. Fab for remote working (if you can't resist a work email) and has, almost, a whole library of books. Sounds like heaven. After a day exploring North Side boutiques or catching a ballgame, kick back on the King-sized bed beneath soaring ceilings, brew a fresh morning coffee, and enjoy a space that feels deeply personal yet professionally supported 24/7.

Time Out tip: Stroll one block over to Southport Avenue to grab a legendary pastry at Crosby's Kitchen or catch an indie film at the historic Music Box Theatre, then hop the scenic Brown Line at Southport station for a panoramic ride straight into the Loop. Read our insider's guide to the best restaurants in Wrigleyville.

Sleeps: Two people.

Perk: This Airbnb comes with temporary guest access to The Metropolitan Club co-working lounge on the 66th floor of the Willis Tower.

Price: From $280 per night.

Neighborhood: The Gold Coast.

When they call it ‘elegant’, they don’t lie. This gorgeous suite is found in the Walton Residence, a historic 1920s building formerly used as the headquarters for Elizabeth Arden in the uparmket Gold Coast area. As befits its former beauty queen status, this one-bedroom apartment doesn’t have a blemish on it. Brazilian hardwood floors, grey velvet sofas, and low-level lighting equal the ideal ambiance for relaxing in a post-Gold Coast shopping spree. You’re in one of Chicago’s fanciest neighborhoods here, and this apartment will make you feel like. Plus, one dog per reservation is allowed.

Time Out tip: Walk two minutes over to Rush Street for prime people-watching and a classic steakhouse dinner at Gibson's, or stroll down Oak Street Beach's paved trail for sweeping Lake Michigan skyline views before catching a Red Line train downtown. Did you know the Gold Coast has its very own beach? 

Sleeps: Four people.

Perk: Indoor fireplace.

Price: From $366 per night.

Neighborhood: Wicker Park. 

This rental’s sure to put a spring in your step – and not just because it’s in an old spring factory. Boasting a pro-level kitchen, an unbeatable collection of rare teas, a Japanese stainless steel soak tub, and endless knick-knacks themed around the building’s industrial past, it’s safe to say there aren’t many (if any) rentals in Chicago quite like this one. If you feel like venturing out, you'll find yourself in the artsy neighborhood of Wicker Park. It has a vibrant food scene, bustling nightlife, and great transit links. What more could you want? 

Time Out tip: Take a five-minute stroll up Division Street to sample vintage vinyl and craft brews at Bangers & Lace, then grab an iced pour-over at Wormhole Coffee before catching the Blue Line straight into downtown or out to O'Hare.

Sleeps: Four people.

Perk: Japanese soaking tub.

Price: From $400 per night.

Do city living right with a stay in this super sleek loft conversion, replete with exposed brickwork and modernist furniture design. Truly aesthetic ways of blending urban cool with indoor comfort. Make the most of good weather with a leisurely breakfast out on the rooftop deck or, if the temperature has dropped (this is Chicago, people) eat the first meal of the day at the attractive wooden breakfast bar. Either way, a top start to the day. Located on the border of Avondale and Irving Park, visitors can take advantage of the free garage parking space before jumping on the Kennedy Expressway to downtown or O’Hare. Great times all around. 

Rooms? One bedroom. Sleeps two guests. 
The mood? An ultra-chic urban oasis. 
Location perks? Set in a calm neighborhood close to Lakeview, known for its dazzling shorefront. Plus, you'll find a wide variety of cuisines and great transit links.  
Budget range? An exceptional vacation home for longer stays at affordable rates. 

Neighborhood: Bucktown.

Chicago’s Bucktown is one of the city’s most vibrant and – in our opinion – fun areas to spend time in. So much so, that it’s good to have somewhere peaceful to recharge in after a busy day spent trawling vintage shops and sipping artisan drinks. That’s why we love this sweet-as-sugar cottage apartment. Exposed brickwork and distressed wood introduce a hipster vibe, while white linens and a big ol’ comfy sofa make things all warm and snuggly. Take your leisurely time getting out of that Pottery Barn California king-size bed in the mornings – we would.

Time Out tip:

Go vintage shopping, followed by cocktail hour, in the nearby Six Corners bar.

Sleeps: Four people.

Perk: Free parking.

Price: From $233 per night.

Situated in the heart of Historic Old town triangle, this gorgeous home is made for vacantioners who are looking for luxury and opulence. Bonus points: You'll be situated on a quiet, tree-lined and secluded street, but still close to a heap of great restaurants, shops, Lincoln Park Zoo, Lake Michigan, Brown Line and more. Oh, and the bathrooms are maybe the real standouts. They feature Carrera marble throughout, towel warmers and heated floors. And, the master bathroom has a soaking tub and multi-head body sprays.

Rooms? Three bedrooms. Sleeps four guests. 
The mood? New money glitz and glamour. 
Location perks? Chow down on a delightful menu prepared by a private chef at your request. 
Budget range? Spenny but well worth the luxury – the ideal spot for anniversaries and family vacations. 

We love to make a grand entrance – and we also love a grand entrance. This shared apartment is divided into private rooms and bathrooms with some rather splendid shared areas in between them. Exhibit A: the mirrored entrance way dominated by a plant-strewn stairway snaking its way up to the loft spaces. Exhibit B: the airy, laid-back kitchen with fresh coffee and vintage poster artworks. Exhibit C: the treasure trove of knickknacks, pictures and furniture found throughout the building. Have we made our case? We think we have.

Rooms? One bedroom. Sleeps two guests.
The mood? Old European bohemianism meets Millennial plant obsession.
Location perks? If you’re fond of a drink come sunset, then River North is your neighborhood.
Budget range? Yes, thankyou, we will take it!

Celebrating a special bride or groom with a group trip to Chicago? Stay in this massive restored Uptown mansion decked out with hardwood floors, eight bedrooms, three living rooms and plenty of parking spots. With three and a half bathrooms, everyone will have space to get ready, plus there’s plenty of lounge space to chill out and wind down and the kitchen is perfect for a pregame.

Rooms? Nine bedrooms. Sleeps 16 or more. 
The mood? Living it up for the weekend in this homey, lavish, and cozy restored mansion.
Location perks? Uptown Chicago is an extremely diverse and vibrant neighborhood – great for architecture, culture, food, and live entertainment. 
Budget range? A luxury stay for a bargain deal when you rally the gang together. 

Indulge your inner rock star at this rococo River North music lover’s abode. Decked out in rock 'n' roll memorabilia and featuring an antique Hi-Fi to play your own tunes, this two-bedroom apartment features other fun touches like a carved wooden canopy bed. Proximity to the CTA Brown and Red lines makes getting anywhere a breeze. You'd imagine someone like Courtney Love or Axl Rose to call this place home, with the luxury-rock vibes throughout. You're also right next to the Loop here too, so it isn't just whistles and bells inside. Free parking too, should it be needed! 

Rooms? Two bedrooms. Sleeps six guests. 
The mood? Rock 'n' Roll chic. 
Location perks? Close to Mag Mile, Michigan Avenue, and Millenium Park or shopping and sightseeing.
Budget range? A decadent, yet budget-friendly group booking.

“Let’s keep things neutral and low-key,” the hosts of this apartment didn’t say when choosing the décor scheme. This studio, in the city’s Gold Coast neighborhood, has a certain old fashioned bachelor pad feel to it. In fact, now we think about it, this place would make a great space to drink an Old Fashioned in. Preferably while wearing a silk dressing gown and reclining in bed. There’s a Red Line station just five-minutes away from the historic building the apartment is in, plus an excellent array of shops and restaurants within walking distance.

Rooms? One bedroom. Sleeps two guests.
The mood? The sound of ice rattling in a heavy-bottomed whiskey glass.
Location perks? Likes large lakes? Then you’ll be pleased with this one…
Budget range? Keep your eye out for discounted rates throughout the year.

This super shiny apartment in ever-popular Lincoln Park combines the best features of an historic building (namely: huge light-loving windows and spacious living quarters) with a freshly renovated interior. We love the underkey Americana at work here. Just a subtle nod to the stars and stripes here, a little wink towards retro living with the baby blue Smeg there… plus there’s all that Space Age silver. They advertise it as a four guest stay, although it’s probably most suitable for a couple or a couple-plus-a-kid, that kind of thing. Extra points for that nice dining table with benches.

Rooms? One bedroom. Sleeps four guests.
The mood? A wholesome vision of urban living.
Location perks? Experience the best of Chicago living with an envy-inducing Lincoln Park address.
Budget range? Should leave you plenty to spend while you’re in town.

Sure, the East Village location (between Wicker Park and West Town) is a cracker when it comes to restaurants, culture, bars, and more, but you might not want to leave this place. Just look at it! There are some high-quality finishes throughout but we’re most stoked about the giant shower and bathtub, and the two private, outdoor decks serving up jaw-dropping views of Chicago. Ridiculous. Hotel who? Live it like a large home-owner this trip.

Rooms? Three bedrooms. Sleeps six guests. 
The mood? An ultra-modern Penthouse with epic skyline views. 
Location perks? Situated on a quiet street that sits close to the Blue Line for easy transit. 
Budget range? A moderately-priced getaway for a group of pals heading to Chi-Town.

If you loved the Cubs before the bandwagon (we put that at about 2016 or so), this Airbnb is for you. Ideal for a sports-filled weekend away, the two-bedroom condo in the heart of Wrigleyville is decked out in crazy Cubbies memorabilia. Seriously—the space features autographed equipment and actual stadium seats. The host's only request: keep your hot dogs and beer cans far away from the white leather sofa.

Rooms? Two bedrooms. Sleeps seven guests. 
The mood? A very stylish ode to the Cubs. 
Location perks? Literally moments away from Wrigley Field, home of the Chicago Cubs in case you didn't know.
Budget range? Get immersed in the Cubs spirit at affordable rates.
Time Out: If you really want to go all out, you need to head to the Cubby Bear bar before the game.

Don't bother trying to find a better view of Chicago than the one from this penthouse. Where contemporary sleek meets sky-high luxury, a stay here comes with access to a private terrace, outdoor pool, hot tub and 24-hour gym. And when you're not distracted by the building's amenities, explore the surrounding culinary scene and nightlife that can be reached within minutes of leaving the apartment. Soak up the natural light streaming in from all angles of this not-so-humble abode, whether you're lounging in front of the flat screen TV or socialising at the breakfast bar. Everything feels deluxe thanks to the spacious rooms, floor to ceiling windows and big double vanity in the bathroom. 

Rooms? Three bedrooms. Sleeps seven guests.
The mood? Uber-modern. 
Location perks? Super central – a short drive to Navy Pier and an hour away from Indiana Dunes National Park if you're up for an adventure. 
Budget range? The views alone are worth blowing the budget for. 

A penthouse with character? This is the place. Combining an industrial and homey aesthetic, the apartment is both stripped-back and full of eclectic touches that bring it to life. The exposed brick and ceiling pipes give it a rustic feel, while the colorful furniture and range of materials provide the warmth and cosiness. The thoughtful design details are what makes this Chicago Aribnb one of the best – a genuine home away from home. The bedrooms have been kept simple so there's no chance of being overstimulated by busy decor before bed. The main bathroom is a haven of white marble, with a jet bath and big shower complete with a seat. The rooftop deck that crowns this 19th-century building is just another reason to book. 

Rooms? Five bedrooms. Sleeps 15 guests. 
The mood? Boho chic. 
Location perks? Next to Magnificent Mile and close to a bunch of nightlife venues from restaurants and comedy clubs to theatres.
Budget range? On the expensive side – best to split between friends. 

The words 'cool' and 'quirky' don't come close to describing the wonder that is 'The Bad Manor' – a design-forward den created as the ultimate escape from reality. The decor is old-school with a mix of period furniture and low lighting to add an air of mystery. Entertain yourselves by looking out for weird details and taking notes on what interior design features to take inspo from for your own home. The bedding has been specially selected to ensure dreamy sleeps all round, with heaters for maximum comfort. Despite it being a self proclaimed 'oasis' there's still Wi-Fi and a TV with multiple streaming platforms if you're not prepared to fully reject reality. 

Rooms? One bedroom. Sleeps three guests. 
The mood? Basement of curiosity. 
Location perks? Avondale was actually named one of the coolest neighborhoods in the world in 2022... by us. The hosts also provide a list of bars and restaurants to help you navigate the surrounding offerings. 
Budget range? Very reasonable.