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

Neighborhood: Logan Square.

You’ve never seen a loft like this one. The Grand Kimball Lodge takes up the top two floors of a century-old former woodworking factory. You’ll be surrounded by exposed brick, timber beams and hardwood floors, and it’s been featured in Architectural Digest'’s list of the best Chicago Airbnbs, plus doubles as a production site for brands like Adidas and Ford when it’s not hosting guests. But the real showstopper is out back: a wood-burning sauna built inside a repurposed shipping container, sitting in a private courtyard with a fire pit and grill. Inside, a 12-person dining table, foosball, an 80-inch smart TV and two huge sofas make it feel like a hangout HQ.

Time Out tip: The building sits right in Logan Square’s arts corridor, so skip ordering in and walk to North Milwaukee Avenue instead, it’s lined with cocktail bars, craft breweries and the century-old Logan Theatre, which still has its original vintage bar.

Sleeps: Four bedrooms, ten beds, three bathrooms. Sleeps 15 guests. 

Perks: Shared wood-burning sauna, private courtyard with fire pit and grill, dedicated workspace, free street parking, foosball and board games.

Price: From $668 a night.

Neighborhood: Humboldt Park.

Before it was an Airbnb, this place was rolling cigars, built in 1908. Now, it’s rehabbed into a stripped-back, brick-walled loft with vaulted ceilings and a working fireplace. It’s detached with no shared walls and no footsteps overhead, just you, the fireplace, and a kitchen island made for people who like to cook on holiday. Head up past the second-floor balcony (hello, treetop views over Humboldt Park) and keep climbing to the rooftop deck, where the whole Chicago skyline shows up to say hello.

Time Out tip: The hosts, who live in the house out front, have put together a great list of nearby spots, including Suncatcher Brewery, Steingold’s Bagels and The California Clipper for cocktails and live music, all within a 15-minute walk. It’s also a short rideshare from Logan Square, Wicker Park and the West Loop if you want to range further.

Sleeps: Three bedrooms. Sleeps 8 guests.

Perks: Private rooftop deck, shared backyard with gas grill and fire pit, working gas fireplace, free street parking, pets allowed.

Price: From $405 a night.

Neighborhood: Pilsen.

This place is the Chicago home of two artists who split their time between here and Tucson, and you can tell the moment you walk in. In the morning, light streams through these really cool, architect-designed walls made of translucent panels and birch plywood, bouncing off glossy black and white floors. There’s a bright, sunshine-yellow room that leads right out to the back porch, perfect for a morning coffee. The vibe inside is eclectic, with plenty of vintage furniture, massive shelves of art books to flip through, and raw 1897 brickwork left completely exposed when they renovated.

Time Out tip: It’s a five-minute walk to Thalia Hall, one of the best small music venues in the city, so it’s worth checking the listings before you book in case there’s a show worth building your trip around.

Sleeps: Two bedrooms (one via a short staircase to an attic room), one bathroom. Sleeps 3 guests.

Perks: Free off-street parking spot, private back porch and backyard with fire pit, dedicated workspace, in-building washer and dryer (free).

Price: From $124 a night.

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 restaurants in West Loop. 

Sleeps: 12 people.

Perk: Full in-unit washer and dryer, dishwasher, dedicated workspace, seven-foot windows facing west for sunset views, six-person dining table plus kitchen island seating.

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.

Perks: Gas fireplace, heated bathroom floors, robes and slippers provided, in-unit washer and dryer, 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.

Perks: Temporary guest access to The Metropolitan Club co-working lounge on the 66th floor of the Willis Tower for stays under 14 days, dedicated workspace, full kitchen, five-minute walk to Wrigley Field and the Brown Line.

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.

Perks: Working indoor fireplace, 24/7 concierge and building staff, private gym in the building, in-unit washer and dryer, one dog per reservation welcome.

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.

Perks: Private hot tub, single-level home with no stairs, in-unit washer and dryer, dedicated workspace, free street parking nearby, stocked bar and rare tea collection.

Price: From $400 per night.

Neighborhood: Avondale, on the border with Irving Park.

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. 

Time Out tip: For dinner, book a table at Anelya on Elston Avenue, James Beard-winning chefs Beverly Kim and Johnny Clark’s modern take on Ukrainian cooking, one of the best reasons to eat in Avondale right now. Reservations go fast, so book around two weeks out, but Saturdays see the most cancellations, so a walk-in has a decent shot then too.

Sleeps: Studio, one bed, one bathroom. Sleeps 2 guests.

Perks: Free garage parking spot, rooftop deck, self check-in, in-building washer and dryer, close to the Blue Line and the Kennedy Expressway.

Price: From $100 a night.

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: Truce, two minutes from the door, is a coffee shop by day and a walk-in-only cocktail bar by night, order the Absinthe Frappe with its pandan whip if it's on the menu.

Sleeps: One bedroom, one bed, one bathroom. Sleeps 4 guests.

Perks: Free street parking, Pottery Barn California king bed, Nespresso and filter coffee makers, five blocks from the Blue Line, steps from Holstein Park.

Price: From $233 a night.

Neighborhood: Old Town Triangle.

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.

Time Out tip: A private chef is available on request for formal or casual settings, so it’s worth booking one in for at least one night if you’re celebrating something. Three bikes with locks are also included free, a genuinely handy way to explore Lincoln Park and the lakefront path without needing a car or an Uber.

Sleeps: Three bedrooms (one queen, one full, one twin), two bathrooms. Sleeps 4 guests.

Perks: Complimentary guest parking permits, two sets of in-building washers and dryers, pet friendly, essential baby gear available on request, private chef available on request.

Price: From $1126 a night. 

Neighborhood: River North.

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! 

Time Out tip: Divvy bikes are right around the corner if you fancy exploring without the car, and hopping the Brown Line across the street gets you to Wrigley Field in about 15 minutes, handy if there's a Cubs game on during your stay.

Sleeps: Two bedrooms, two beds, two bathrooms. 

Perks: Free dedicated parking spot, dedicated workspace, well-trained dogs welcome, full cable and HBO on the 65" TV.

Price: From $608 a night.

Neighborhood: Gold Coast.

“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.

Time Out tip: Skip driving altogether, the neighbourhood is walkable and everything from Oak Street Beach to the Mag Mile is within easy reach on foot or a short Uber. If you do need to park, book ahead through SpotHero rather than circling for street parking, evenings and event days get competitive fast around here.

Sleeps: Studio, one bed, one bathroom. Sleeps 2 guests.

Perks: Free in-building washer and dryer, dedicated workspace, radiant heating, five-minute walk to the Clark/Division Red Line.

Price: From $358 a night.

Neighborhood: Lincoln Park.

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.

Time Out tip: Skip street parking stress altogether, the host provides free residential parking stickers on arrival, and there's a garage space available for $20 a night with free EV charging if you’re driving electric.

Sleeps: One bedroom (studio layout), one bed, one bathroom. 

Perks: In-unit washer and dryer, dishwasher, free residential parking permits, paid garage parking with EV charger, welcome cookies from the host.

Price: From $338 a night.

Neighborhood: Wrigleyville.

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.

Time Out tip: If you really want to go all out, head to the Cubby Bear bar before the game. Also worth knowing: on game or event days you’ll need to move your car out of the lot or pay the event parking fee, typically $40 to $100 per car, so factor that into your budget if you’re driving.

Sleeps: Two bedrooms, two beds plus a trifold mattress and a modular sofa that converts to a queen. Sleeps 7 guests.

Perks: Two private entrances with patio space, in-unit washer and dryer, central AC, single-level with no stairs, free on-site parking (subject to event-day fees).

Price: From $269 a night.

Neighborhood: River West.

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 socializing at the breakfast bar. Everything feels deluxe thanks to the spacious rooms, floor to ceiling windows and big double vanity in the bathroom. 

Time Out tip: Book with a group that’ll use the building amenities—the outdoor pool, hot tub and party room with a commercial demonstration kitchen are all there to use. Just know some of these are seasonal and may carry extra fees, so check what's open when you're staying.

Sleeps: Three bedrooms, four beds (two king rooms, one queen, plus a rollaway), three bathrooms. Sleeps 7 guests.

Perks: 24-hour gym and building amenities, outdoor pool and hot tub, EV charging, Sonos sound system, single-level with no stairs.

Price: From $1085 a night.

Neighborhood: Old Town.

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. 

Time Out tip: Brace for the climb, there are 45 steps across two flights to reach the unit with no elevator, so plan accordingly if anyone in your group has mobility concerns or you’re hauling a lot of luggage. The comedy clubs Zanies and Second City are both a short walk away, worth booking ahead if you want a good night out with the group.

Sleeps: Five bedrooms, eight beds. Sleeps 15 guests.

Perks: Private rooftop deck with grill and 360-degree skyline views, two full kitchens and living rooms, two push-button fireplaces, vintage pool table and dartboard, pet friendly.

Price: From $2230 a night.

Neighbourhood: Avondale.

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. 

Time Out tip: Avondale was actually named one of the 20 coolest neighbourhoods in the world in 2022, by us. The hosts also hand over a list of their own favourite bars and restaurants nearby, worth asking for on arrival if you want to skip the guesswork.

Sleeps: One bedroom, two beds. Sleeps 3 guests.

Perks: Free on-site parking, dedicated workspace, dedicated heaters in bedroom and bathroom, sound machines for light sleepers, air fryer in place of an oven.

Price: From $315 a night.

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