Marcy Miniano
Shanne GanAnyone who has been to Chicago would agree that the Windy City has plenty to offer; whether it’s trying the popular deep-dish pizza or visiting Millennium Park for a photo with The Bean! In fact, some of you might’ve been curious about it after watching the hit Hulu series, The Bear. As the third-largest city in the United States, Chicago is known for its incredible architectural marvels — including the world’s first skyscraper. Hence, it’s only fitting that the best Chicago Airbnb picks are just as impressive!
Read on for a list of every Airbnb in Chicago, Illinois that will make you want to stay longer.
Also read: 20 Stunning Airbnbs in Los Angeles That You’ll Want to Live In
Top-rated Chicago Airbnb stays to book
1. This stylish artist’s loft in the West Loop
Listing name: Explore the West Loop from an Artist’s Loft
Listing type: Entire loft
Max. no. of guests: 6
No. of bedrooms: 2
Located near the heart of West Loop in Downtown Chicago, you’ll find that everything you need is within walking distance of this industrial loft. The bustling enclave is a favourite among tourists and locals for being a foodie mecca. In fact, the place is within walking distance of plenty of shops and restaurants.
The loft has a simple yet artful design, with curated art pieces found throughout the apartment. Spacious and comfortable, it’s the best Airbnb in Chicago downtown for a group of friends or a family!
2. This incredible Wicker Park home with a grungey vibe
Listing name: Tea Studio in Wicker Park Spring Factory
Listing type: Entire loft
Max. no. of guests: 2
No. of bedrooms: 1
This vacation rental called Tea Studio looks every bit fascinating, thanks to its grunge-industrial interior with a splash of Japanese influences. Meanwhile, the mix of wood and earthy tones results in a space that’s roomy yet cosy. Overall, it’s a study in maximalism without being too eccentric, and we’re here for it!
It’s also conveniently located in Wicker Park — aka one of Chicago’s trendiest neighbourhoods. Find anything from coffee shops to boutiques around the area, where public transport is also easily accessible. After a day of exploring the vibrant surroundings, whip up a storm in this loft’s professional-grade kitchen, or relax in the Japanese soaking tub.
3. This whitewashed flat with rustic and retro elements
Listing name: Explore Chicago from an Urban Sanctuary with Free Parking
Listing type: Entire rental unit
Max. no. of guests: 2
No. of bedrooms: 1
Baseball fans will love this pristine studio because it’s only a 10-minute drive to Wrigley Field: home of the Chicago Cubs! Set between South Old Irving Park and Kilbourn Park, here is where you can experience living in one of the city’s oldest neighbourhoods. Experience traces of what these used to be like, while exploring various eateries and shops. Fancy a drink or two? Don’t miss out on the craft beer taverns and cocktail bars along North Milwaukee Avenue.
After a long day, relax in this Chicago Airbnb that comes complete with comforting amenities and retro-minimalist decor. Personally, we can’t get enough of the hanging lounge chair and the outdoor deck!
4. This eclectic Airbnb in the Chicago Arts District
Listing name: Eclectic Artist Designed Sanctuary Heart of Pilsen
Listing type: Entire rental unit
Max. no. of guests: 4
No. of bedrooms: 2
There’s no better way to immerse yourself in the city’s creative scene than staying in Pilsen (aka the Chicago Arts District)! The vibrant neighbourhood is the place for music, art, and food lovers. And this apartment captures the neighbourhood’s essence! Think intentionally mismatched artworks and eclectic colours that are anything but basic. Fun fact: The Hosts are actually an artist couple — how cool is that?
When exploring the area, you can expect a fun selection of Instagram-worthy street art, vintage clothing shops, and artisan furniture stores. Want to venture further? The nearest train station and bus stop are both just a few blocks away!
5. This penthouse that has been featured in architectural magazines
Listing name: Stay in a Designer Penthouse with Art Gallery
Listing type: Entire condo
Max. no. of guests: 8
No. of bedrooms: 3
We bet you won’t find anything quite like this spunky designer home. Arguably the most unique Chicago Airbnb, it boasts an amazing collection of contemporary artworks. And we’re not just talking about the usual paintings on the walls, but even sculptures and installations by emerging artists — all curated by the Host who happens to be a designer and gallerist!
Exploring the city on foot does get exhausting so this one is perfect, with public transport being easily accessible. The Chicago Avenue Blue Line subway stop is only half a block away, while the buses can take you downtown in minutes. You may also choose to unwind within the confines of this condo, which comes with a private patio and an extensive record collection.
6. This rock ‘n’ roll-themed Airbnb in River North
Listing name: River North’s Rock N Roll – Covd Safer, No Common Areas
Listing type: Entire flat
Max. no. of guests: 8
No. of bedrooms: 3
Staying home can also be an experience in itself with this rock ‘n’ roll-inspired Airbnb in Chicago! The home is decorated with memorabilia in the form of posters and guitars that will make you feel like a rockstar. There’s even a life-size cut-out of Elvis Presley in the living room!
You’ll find this in River North, one of Chicago’s oldest and liveliest neighbourhoods. When exploring the area, you can expect a mix of everything from decades-old eateries to art galleries. Fans of The Bear will also be pleased to know that this is where most of the show takes place! (Although, we can’t promise a run-in with Carmy and Sydney).
7. This cute, pet-friendly studio in West Humboldt Park
Listing name: Checkerboard Studio with Private Outdoor Hot Tub and Yard
Listing type: Entire rental unit
Max. no. of guests: 2
No. of bedrooms: 1
This comfy apartment features subtly rustic decor and plenty of space for two. Think faux-fur upholstery and vintage-looking furniture juxtaposed with a dominantly white palette. Pets are also welcome here, and the place even has a private yard for your furry friends to play in.
You’ll find this in West Humboldt Park, a culturally diverse area filled with public green spaces and historic homes. Other neighbourhoods like Wicker Park and Logan Square are just a stone’s throw away for those who wish to try out more restaurants and bars at night.
8. This spacious brick penthouse with rooftop views
Listing name: Stunning Old Town Penthouse with Private Rooftop
Listing type: Entire loft
Max. no. of guests: 16+
No. of bedrooms: 5
Vacationing with your extended family or a large part of friends? You’ll have to bookmark this massive Chicago Airbnb. The five-bedroom loft features a mix of old and new, with its contemporary decor contrasting the exposed brick walls and barnwood floors. A private rooftop is also yours to throw a rooftop party anytime you want.
The penthouse is located in Old Town: a historic neighbourhood famous for the buildings from the Victorian era. It’s also close to the Magnificent Mile, aka Chicago’s shopping paradise!
9. This five-bedroom factory loft with a screening room
Listing name: Modern Loft Duplex in a 1904 Former Factory
Listing type: Entire loft
Max. no. of guests: 8
No. of bedrooms: 3
With decorative pops of colour, this gorgeous loft in River West will have you whipping out your phone for photos the minute you enter. Since it used to be a picture frame factory back in the early 1900s, one can expect high ceilings and industrial elements that make it look effortlessly cool. Oh, and did we mention it comes with a pool table and a screening room?
Two minutes is all you need to get to the nearest bus stop or train station if you’re staying in this Airbnb in Chicago. In fact, its location is so convenient that you can even get to the famous Wicker Park on foot.
10. This Logan Square apartment with fun-filled amenities
Listing name: Fun & cozy getaway w/POOL/game room/FREE parking
Listing type: Entire rental unit
Max. no. of guests: 6
No. of bedrooms: 1
How about a Chicago Airbnb with a pool and other amenities to keep you entertained? This pastel-painted flat in Logan Square is the way to go. The living room connects to a TV/game room. There, you’ll find over 30 board games, as well as an electronic dart board and a token slot machine (don’t worry — the Host provides the tokens). Meanwhile, the kitchen comes with pool-safe glassware, portable tables that you can use anywhere in the house, a coffee machine, and even a Margaritaville Tahiti Frozen Drink Machine!
While it only has one bedroom, the space can accommodate up to six guests. The living room and TV/game room each have a plush sleeper sofa large enough for two. Other attractive features include a jacuzzi in the bathroom, a rowing machine for cardio workouts, and a shared outdoor deck.
11. This speakeasy-inspired Airbnb in Chicago South Side
Listing name: Ground-Level Speakeasy: 1BR-1.5BA Near Everything!
Listing type: Entire rental unit
Max. no. of guests: 2
No. of bedrooms: 1
Stepping into this elegant apartment feels like being a movie set in the Prohibition era; with its Art Deco walls and furniture, ambient lighting with dimmable settings, and wet bar. It also comes with a private full-body gym, a dedicated workspace, and a 65-inch TV with streaming channels.
The home pays homage to the African-American culture through the stunning mural in the living area. After all, it’s located in Bronzeville: a historically Black neighbourhood in Chicago’s South Side. That said, you can expect a mouth-watering selection of BBQ and soul food restaurants in the area! Other nearby attractions include the Museum Campus and Hyde Park.
12. This gorgeous flat in a historic Lincoln Park townhouse
Listing name: The Best of Lincoln Park!
Listing type: Entire rental unit
Max. no. of guests: 4
No. of bedrooms: 2
Travellers who are into the “quiet luxury” aesthetic should opt for this Airbnb in Lincoln Park, Chicago. It looks every bit dreamy and cosy, with its tall arched windows, well-curated furniture, and ample space that invites you to unwind after a long day of touring! Further making you feel at home is the kitchen, which features a sleek granite counter and state-of-the-art appliances. Also, you might want to call dibs on the main bedroom, which has a private deck with a view of the picturesque neighbourhood.
Speaking of the neighbourhood, there are definitely plenty of spots worth checking out. The list includes (but isn’t limited to) Lincoln Park Zoo, Lincoln Park Conservatory, South Pond, North Avenue Beach, and Chicago History Museum.
13. This contemporary-minimalist condo with a balcony
Listing name: 2BR Chic New Apartment With Rooftop Pool & Gym
Listing type: Entire rental unit
Max. no. of guests: 6
No. of bedrooms: 2
This family-friendly flat is all about understated luxury, with its sleek furniture and fixtures and bright pops of colour that make it look every bit stylish. It features an in-unit washer and dryer, a fully equipped kitchen, and walk-in closets, making it ideal for big groups who are looking to stay in Chicago longer. But perhaps our favourite features would be the balcony and floor-to-ceiling windows that allow plenty of natural light.
Since it’s an Airbnb in Downtown Chicago with a balcony, you can expect proximity to top attractions as well as great views. Not to mention, it’s in a condo building that has a rooftop lounge, a gym, and a swimming pool. What more can you ask for?
14. This family-friendly apartment in Irving Park
Listing name: Cool and Modern Chicago Apartment near Transit
Listing type: Entire rental unit
Max. no. of guests: 5
No. of bedrooms: 3
This Chicago Airbnb is a popular pick for those who enjoy a simple yet stylish home. Located in Irving Park, it provides easy access to other popular neighbourhoods in the city via public transport. It’s also less than a 30-minute drive from Chicago O’Hare International Airport. What’s more, the nearest convenience store can be easily reached on foot.
Beyond the fully equipped kitchen and stocked bathrooms, this apartment also comes with a washer and dryer for those who prefer packing light. One thing’s for sure: You’ll definitely feel right at home here!
Also read: 22 Best Beach Houses to Book on Airbnb, From California to Hawaii
As evident in the list above, Chicago’s homes are nothing short of exceptional. Which Airbnb in Chicago will you pick for your trip to Chi-Town? Let us know by tagging us in your photos when your trip pushes through!
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