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The 12 best Airbnb lofts in Chicago

These loft homes boast high ceilings, plenty of light and spacious floor plans

Written by
Morgan Olsen
Alex Floyd-Douglass
Jennifer Banful

It's no wonder that Chicago developers started flocking to the city's rich industrial infrastructure in the 1980s. The massive, window-lined buildings make beautiful condo conversions that attract hip city-dwellers looking for something different. Neighborhoods like the West Loop, South Loop, and Logan Square offer converted lofts that check all the right boxes with soaring ceilings, open floor plans, massive windows, and exposed brick and timber galore.

Whether you're planning a staycation or getting away to Chicago for the weekend, a converted space could be the perfect fit if you love urban and industrial vibes. Check out our picks of the best and most amazing lofts on Airbnb. You're welcome.

🛏Looking for unique Airbnbs in Chicago?
💞Check out the most romantic hotels in Chicago

Who makes the cut? While we might not stay in and review every Airbnb featured, we've based our list on our expert knowledge of the destination covered, editorial reviews, user reviews, hotel amenities and in-depth research to find you the best stays. This article includes affiliate links. These links have no influence on our editorial content. For more information, see our affiliate guidelines.

Best Chicago Airbnb lofts

The penthouse with private rooftop in Old Town
Courtesy: Airbnb

1. The penthouse with private rooftop in Old Town

This gorgeous penthouse loft Airbnb is perfect for larger groups, sleeping up to 16 guests in five bedrooms. It's the ideal place for those wanting to explore the fun side of the town whilst also being surrounded by culture and having some well-deserved R&R. Built in 1897, the Airbnb has been renovated to allow the exposed brick, 20-foot ceilings, and 120-year-old barn wood floors to give you some comfort. You'll have access to your own private roof terrace that has stunning views of the city's skyline - the best place to enjoy a glass of wine and watch the sunset on the horizon. You'll have everything you need for a comfortable stay, including modern amenities like a fully-equipped kitchen, bathroom with hot tub, rainforest dual shower, and two fireplaces; just to name a few. There's also a vintage pool table, dartboard, and surround sound system to help keep you entertained.

Rooms? Five. Sleeps 16+ guests.
Mood? High-ceilinged wonder.
Location perks? In the heart of Old Town.
Budget range? Spennnnny.

The tea studio in Wicker Park Spring Factory
Supplied by Airbnb

2. The tea studio in Wicker Park Spring Factory

It can't get any better than this tea studio Airbnb that looks like something out of a design magazine. While it doesn't come cheap, it's definitely worth splurging on. Here, you can relax in a one-of-a-kind former spring factory with Chicago's trendiest neighborhood at your doorstep. You'll be steps away from an abundance of cool coffee shops, boutiques, bookstores, cocktail bars, and restaurants. Wicker Park stands out for its diversity, walkability, and unique character so there is definitely something here for everyone.

Rooms? One. Sleeps two guests.
Mood? Industrial chic.
Location perks? Nestled in Chicago's 'trendiest' neighborhood. Enjoy the vibes.
Budget range? Very affordable.

The entertainment home in Logan Square
Photograph: Courtesy Airbnb

3. The entertainment home in Logan Square

This seven-bedroom, 5,307-square-foot abode is the ultimate crashing pad for big groups and has even hosted weddings, pop-up events, and reunions. The centerpiece of the common space is a tricked-out chef's kitchen with plenty of seating for visiting guests. Cool details—like a smoke stack stairway leading to the master bedroom—make this Logan Square rental an unforgettable stay.

Rooms? Six. Sleeps 16+ guests.
Mood? Factory fun.
Location perks? Perfectly located between three neighborhoods with endless bars, cafes, and restaurants to choose from. 
Budget range? Pricey but totally worth it for the right event.

The funky artist's loft in River North
Photograph: Courtesy Airbnb

4. The funky artist's loft in River North

Spend less when you rent a private room within this sun-drenched artist's loft. Conveniently located in River North, the apartment is decorated in plants, Oriental rugs, and tons of artwork. Bookmark this rental for summer so that you can enjoy the 60-foot outdoor deck that offers stellar views of the city.

Rooms? One. Sleeps three guests.
Mood? Artsy vibes.
Location perks? Head out onto the private terrace and soak up the sweeping city views.
Budget range? Insanely cheap.

The modern stunner in River West
Photograph: Courtesy Airbnb

5. The modern stunner in River West

This seriously chic loft is surrounded by some of Chicago's hippest neighborhoods like West Loop, West Town, and Noble Square, making it easy to hop around and see more throughout your stay. The host has a strict policy against bachelor and bachelorette parties, but the sunny three-bedroom apartment makes an ideal backdrop for a quiet weekend in with a small group of friends.

Rooms? Three. Sleeps 12 guests.
Mood? Designer loft.
Location perks? Steps away from the Blue Line and what the rest of the city has to offer.
Budget range? As spenny as you'd expect.

The urban glam home in West Town
Supplied by Airbnb

6. The urban glam home in West Town

If you're looking to enjoy loft life on a budget, but not have to compromise on space, consider this loft space in the heart of West Town. It's decked out with pretty plants, chic grey sofas, and wooden finishes. It's also located on the top floor which means you'll be guaranteed lots of natural sunlight. The best part. Plus, the major commercial street is one block away and has plenty of good restaurants and an easy bus into downtown.

Rooms? Two. Sleeps four guests.
Mood? Open-plan living.
Location perks? In the heart of West Town.
Budget range? So cheap.

The trendy loft in Wicker Park
Supplied by Airbnb

7. The trendy loft in Wicker Park

This antique-style loft is just full of character and charm, it's a three-bedroom If you're looking for a personality-filled pad, this three-bedroom charmer with mid-century modern furniture, open brick walls, and spacious bedrooms. It's also newly refurbished and designed specifically for larger groups to enjoy the space in comfort. So grab your family or some of your closest friends and make that booking – and picture yourself having chilled nights at the BYOB lounge.

Rooms? Three. Sleeps eight guests.
Mood? NYC loft vibes.
Location perks? In the uber cool Wicker Park area.
Budget range? On the pricier side of things. 

The sunny loft in Forest Park
Photograph: Courtesy Airbnb

8. The sunny loft in Forest Park

Stay just outside the city when you book a stay at this affordable two-bedroom, two-bathroom condo in Forest Park. The newly remodeled loft is situated on the top floor of a former Masonic temple, and the original timber ceilings and beams are still intact. To sweeten the deal, there's a Blue Line stop just three blocks away, making it possible to be downtown in less than 30 minutes.

Rooms? Two. Sleeps four guests.
Mood? All round zenergy.
Location perks? In central Forest Park, where restaurants are claimed to be the 'best in neighborhood dining' in Chicago.
Budget range? An absolute steal.

The cool compound in Logan Square
Photograph: Courtesy Airbnb

9. The cool compound in Logan Square

This bi-level hidden gem offers 2,000 square feet of space in Logan Square. The main floor, which houses the kitchen and living space, is partially subterranean but still gets plenty of sunshine. Climb the atrium Italian staircase to get to the second floor, where you'll find the master bedroom, a private balcony, and a fireplace.

Rooms? Two. Sleeps five guests.
Mood? Hidden oasis.
Location perks? Located in Logan Square, a block away from Milwaukee's shops and restaurants.
Budget range? Pricey but works out well for a month's stay for a group.

The modern one-bed in South Loop
Courtesy: Airbnb

10. The modern one-bed in South Loop

Seriously, who would have guessed that this flashy loft apartment was once a post office in a former life? Yep. This place went from a drib drab sorting room to an uber-calm and contemporary one-bed oasis with a whole heap of space. That's some facelift! Not to mention you're just Steps away from Grant Park (or as they call it, Chicagos Front Yard) and Printers Row (a.k.a South Loop) for historic architecture and delicious cheap eats like Flacos Tacos.

Rooms? One. Sleeps four. 
Mood? Modern and clean. 
Location perks? Situated near Grant Park.  
Budget range? A pretty penny for a cool and contemporary pad. 

The artsy one in River North
Courtesy: Airbnb

11. The artsy one in River North

If you're after something a little more, say, out of the ordinary, aren't fussed about sharing communal areas, or just want to save a few bucks, this private room in this artsy loft will do the trick. The room features a king-size bed, a private bathroom, and, instead of walls (or doors for that matter), there are curtains on either side, making the space feel incredibly open – pretty cool, as long you dig the commune vibes and skip the hanky panky ...When you need a change of scenery, there's the rooftop garden and a tonne of awesome art galleries, bars and restaurants just a few blocks away – the perfect retreat for creatives.

Rooms? One. Sleeps three. 
Mood? Vintage art deco vibes.
Location perks? There's so much art at your disposal both inside and outside of this trendy loft.
Budget range? Pretty cheap for a typical four-night stay
Time Out tip: Check out the Art on the Mart for incredible digital installations by the river. 

The Roomy Loft in Wicker Park
Courtesy: Airbnb

12. The Roomy Loft in Wicker Park

The stained glass window says it all when it comes to staying at this retro apartment in Wicker Park. The vibe here is super laid-back with tonnes of space to create, so it's no wonder artists like to take up residence in the studio on the 1st floor. The loft is big enough to sleep five and comes equipped with a full kitchen, an open lounge, and dining area, making it a great base to explore the trendsetting Wicker Park and Bucktown neighborhoods. 

Rooms? One. Sleeps five.
Mood? The artist's cave. 
Location perks? An easy 10-minute stroll to the Blue Line train for access to the airport.
Budget range? An affordable stay with lots of intrigue. 


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