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

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. 

Rooms? Three bedrooms. Sleeps up to 12 guests. 
The mood? A trendy apartment with industrial vibes throughout. 
Location perks? Slap bang in the middle of the former warehouse district Fulton Market with restaurants, cafes, and bars all on your doorstep. 
Budget range? Mid-range – a great option for large groups.   

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. 

Rooms? One bedroom. Sleeps two guests. 
The mood? A trendy apartment with industrial vibes throughout. 
Location perks? Tucked away on a quiet residential street in Lincoln Park, just a short stroll to the nearby lakefront and Lincoln Park Zoo. 
Budget range? Affordably priced for a typical three-night stay; an ideal location for couples. 

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. Sleeping two guests in a cozy king-sized bed, you can fall in love all over again with a romantic trip for two, or have a bit of a self-care staycation after the stresses of normal life. Fab for remote working (if you can't resist a work email) and has, almost, a whole library of books. Sounds like heaven. 

Rooms? One bedroom. Sleeps two guests. 
The mood? The space is a mix of retro, modern and sultry vibes – in other words, very chic. 
Location perks? A short walk to Wrigley Field, Southport Corridor and Metro Theatre. 
Budget range? A luxury couple's stay in one of Chicago's best spots. 

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. 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 most upmarket neighborhoods here, and this apartment will make you feel like.

Rooms? One bedroom. Sleeps two guests.
The Mood? Hotel-level polish in a place that feels like home.
Location Perks? Live the Gold Coast high life in one of Chicago’s most upmarket (and fun) neighborhoods.
Budget Range? Affordable luxury.
Time Out tip: Roam the local streets to get a feel for the amazing breadth of historic architecture this area is famous for.

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.  

Rooms? One bedroom. Sleeps two guests. 
The mood? An ultra-cool studio with sleek furnishings.
Location perks? An artsy neighborhood with a vibrant food scene, bustling nightlife, and great transit links. What more could you want? 
Budget range? This trendy spot is on the luxury end. Ideal for short city breaks. 

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. 

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.

Rooms? One bedroom. Sleeps four guests.
The Mood? A cute slice of cottage life in the heart of the city.
Location Perks? You’ll be bedding down in Bucktown, Chicago’s liveliest and artsy-ist areas.
Budget Range? Split between four, this is a steal.
Time Out tip: Go vintage shopping, followed by cocktail hour, in the nearby Six Corners bar.

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. 

Head just outside of the city for a truly unique stay on a micro-flower farm. Outside, you’ll find a pocket forest, fruit trees, a kids' play house, and, yes, flowers. Inside, it’s a brilliant mix of warming vintage kookiness and delicious luxury. For those looking for the latter, check out that massive four-poster bed, the hot tub, and the carefully selected goodies in the bathroom. There’s a proper workstation set up here but if you’re very much not WFH this holiday, that antique bar and cocktail shaker might be more your thing.

Rooms? Two bedrooms. Sleeps seven guests.
The Mood? Beautiful eco-conscious cottagecore decor vibes with flowers, flowers, and more flowers.
Location Perks? It's just 30 minutes to Downtown, but do spend time in the lovely, leafy, friendly world of Berwyn where you'll find the legendary Fitzgerald's Nightclub.
Budget Range? Absolute bargain for such a lovely place.
Time Out tip: This one’s a total gem for families with little ones. The hosts have even set up a baby room with a crib and monitors, books, and toys. 

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.

Make your trip a lavish one with this lush apartment in Lincoln Park, just a block away from the Zoo and strolling distance from a handful of mindblowing – they call it Windy City, after all – selection of restaurants and bars for all your culinary cravings. The vibe here is old-fashioned with a modern spin – expect classic touches like dark wood furnishings and French doors, in contrast with bright walls lined with cool contemporary art. The space is ideal for 

Rooms? Two bedrooms. Sleeps four guests. 
The mood? A modern apartment with an old-timey swagger.
Location perks? Swoon over the array of tropical plants on display at Lincoln Park Conservatory, a short walk from the Airbnb. 
Budget range? In the mid-high ranges for something a little more elevated in style.

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.