10 Best Airbnb Monthly Rentals In Chicago, Illinois - Updated 2025

Aarti
Contributing Writer
Updated
| 4 min read

Situated on Lake Michigan in Illinois, Chicago, also known as the Windy City, is one of the largest cities in the United States. It is notable for its amazing skyline that boasts some of the tallest skyscrapers in the country, including the Willis Tower and John Hancock Center. If you’re interested in learning about the local history and art, you must include Museum of Contemporary Art and Oriental Institute Museum in your list of places to visit in Chicago. The city also has more to offer such as Jackson Park, Oak Street Beach, and Chicago Riverwalk, among others. Due to its vastness, Chicago is hard to explore within a few days. That’s why tourists usually choose hotels with free parking in downtown Chicago or accommodations that offer monthly rentals. For quaint vacation homes, continue reading for the best Airbnb monthly rentals in Chicago, Illinois.

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on February 04, 2025.

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1. Aesthetically decorated home with modern furnishings

If you’re looking to have a fun yet peaceful vacation, you must check out this beautiful Airbnb rental. Oozing with style, this three-bedroom home is built with keeping minimalism in mind. Featuring modern furnishings, guests can make use of amenities such as free parking on the premises, free wifi, and a dedicated workspace that can make it easier to have a comfortable vacation. It also features a fully equipped kitchen, and a flat-screen TV in the living room for your entertainment.

Stayed at this property?
Chicago, Illinois, United States

10.22 km (6.4 mi) from Ping Tom Memorial Park
263 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 3 Beds 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Host:
they were the perfect host
hosts were super responsive
hosts were responsive and kind too
hosts were readily available and kind
she was understanding and kind
Location:
it is located in a great neighbourhood
nice location and nice place
great location beautiful comfy space
also very close to some wonderful mexican restaurants that deliver late night
it was reasonable and close to some cool venues
Cleanliness:
clean and comfortable stay
clean and nicely decorated house
was very clean and homey
everything was truly clean and comfortable
clean chic and comfy
Amenities & Room:
smart tv was complete with sling netflix amazon etc
beds and bedding were perfect
visited during winter but the heater was very nice and kept us both warm
bed were super comfortable
paige and nathan's main floor apartment was perfect for our visit to chicago
Read more reviews

2. Modern rental for three (from USD 60)

It can be tricky to find long-term Airbnb rentals in Chicago, Illinois, that are bright, spacious, closer to conveniences, and also in a great neighborhood. And this home checks all the boxes. It is situated in the Pilsen neighborhood, which according to Forbes is one of the 12 coolest neighborhoods in the world. Additionally, it is a newly renovated, two-bedroom apartment that comes complete with a bathroom, a living room, and a kitchen. This long-term Airbnb rental in Chicago exudes a contemporary vibe, thanks to all the art pieces scattered around the apartment.

Stayed at this property?
Chicago, Illinois, United States

1.99 km (1.3 mi) from Ping Tom Memorial Park
287 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 3 Guests 2 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Host:
she is a very good host
this place was lovely and the host just as kind
audra was an amazing host she was very hospitable and prompt response
if you're sensitive to noise you can definitely hear everything above you since the host lives there
an amazing host will definitely stay there again
Location:
i enjoyed the neighborhood so close to everything
super spacious place near lots of restaurants
the location is close to public transit and a hop-skip away from chicago's major attractions
we were within walking distance of great restaurants and bars
there’s also good places to eat within walking distance and it’s so close to downtown
Cleanliness:
the space was clean and cozy
very clean stylish and comfortable
great modern space very clean and comfortable
the interior is very clean and modern
very clean well-appointed apartment in a terrific neighborhood
Amenities & Room:
enjoyed the nice little patio and cool a/c
this is a very nice apartment with all the necessary appliances and spaces for a pleasant stay
this place is great i'm pretty picky about beds and i thought the mattress was comfy
the kitchen is so well equipped which makes cooking for yourselves easy if you want to
the space was beautiful and comfortable
Read more reviews
Monthly discount: 40% off

3. Two-bedroom home within a historic building (from USD 114)

Going to Chicago for a month or maybe two? This two-bedroom condo is brand new and is the perfect place to rest and stay. Book this condo that is ideal for up to six guests. Within the property, the space boasts elegant furnishings and decor, and it comes complete with a living room with a flat-screen TV, a full kitchen, one bathroom, and a dining area. Located close to the University of Chicago, the property is within a walking distance from lakefront beaches, golf courses, and more.

Stayed at this property?
Chicago, Illinois, United States

8.56 km (5.4 mi) from Ping Tom Memorial Park
224 reviews   Superhost Wifi Available
ENTIRE CONDO 3 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Host:
very responsive host
very thoughtful host who went the extra mile
very nice and convenient flat with a careful owner that answers very quickly and is very helpful when requested
puppy quite friendly that lives upstairs
luke is a great host and checked into make sure we had everything we needed
Location:
great location for visiting u chicago
great location in hyde park a few blocks from campus
the location was fantastic and luke was thoughtful in offering snacks for us
very close to the jewel grocery store
location location location great for uc campus access and provisions/restaurants nearby
Cleanliness:
clean comfortable place
it was so clean and cozy
plenty of clean towels and extra blankets
the apartment is clean and convenient
this condominium was very clean and comfortable
Amenities & Room:
we had room to spread out and relax
we had everything we needed for our stay plenty of linen and comfortable beds
wonderful welcoming super clean and larger than expected apartment literally across the street from uchicago's south campus residence hall
the apartment is big with plenty of space to relax
wifi worked perfectly and all the info we needed was readily available
Read more reviews
Monthly discount: 20% off

4. h-century Pullman workers flat for three guests (from USD 1844)

This house, situated in the heart of Pullman Landmark District, is suitable for those with creative minds wanting to explore Chicago. Should you choose to spend time indoors, the property offers enough modern amenities that will keep you snug and comfortable, thanks to the double bed, airbed, free parking on premises, a dedicated workspace, and a full kitchen. The rental also comes with a backyard with a seasonal salad garden, and washer and dryer, so guests don’t even have to worry about what to do with their dirty clothes.

Stayed at this property?
Chicago, Illinois, United States

18.92 km (11.8 mi) from Ping Tom Memorial Park
320 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
jb is a great host and is prompt with responses
jb was a wonderful host absolutely gorgeous space
jb is a wonderful host (and a talented artist himself)
jb is a very pleasant host
jb was an excellent host very attentive and communicative - everything went very smoothly
Location:
great place in a cute neighborhood
beautiful unique location in historic pullman
also super close to the train to go downtown
the location is terrific with convenient access to the metra
great quiet location in a wonderfully historic apartment
Cleanliness:
its a clean clean clean place
the bed was clean and comfortable
really unique and clean space in a historic neighborhood
the neighbors were all very friendly and the apartment was clean and comfortable
this place was fantastic to stay at very unique clean and quiet
Amenities & Room:
cozy house with really cool decor and great amenities
was worried at sight of small double bed but the comfort had me sleeping like a baby
it was nice to have a full working kitchen to save money on meals
jb’s apartment was absolutely perfect
the beds were comfortable and everything was in great shape for our visit
Read more reviews
Monthly discount: 50% off

5. Well-appointed rental on the main road (from USD 93)

This cozy home on the first floor offers one bedroom and one bathroom that is ideal for couples, solo travelers, or business travelers. Guests staying here get access to everything within the rental: a fully equipped kitchen, a dining area, a living room with a smart TV, and a full-size bedroom. You can even make use of the garage parking at an additional cost if you’re bringing a car during your long-term stay in Chicago. However, if you plan to commute, the bus stop is easily accessible because of the property’s location on the main road.

Stayed at this property?
Chicago, Illinois, United States

8.35 km (5.2 mi) from Ping Tom Memorial Park
241 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 6 Guests 1 Bedroom 1 Bathroom

Accommodates: 6

Top guest reviews
Host:
host was very friendly and helpful
the host was very professional amd friendly
fortino was such a great host timely responses so helpful when answering our questions
great host will definitely be booking again
amazing stay host is great and fast response
Location:
i liked the location
good place for stay good location everything is near
perfect location close to the airport and nice and cozy
the place was really nice and the location was near to the metro station
very convenient location near the city and great restaurants
Cleanliness:
clean and quick on responding
place was very clean parking was better than expected
i was very clean he gave us a lot of location tips and the communication was good
place is super comfy and clean
super clean and comfortable apartment was actually sad to leave it because it felt so cozy i loved it
Amenities & Room:
comfortable bed nice shower spacious closet space
fortino’s place was comfortable and had everything we needed
he was super responsive to my messages and provided a lot of details that helped my stay comfortable
Read more reviews
Monthly discount: 10% off

6. Cozy apartment close to the public transport (from USD 90)

This one-bedroom apartment is situated close to different restaurants, food markets, cafes, shopping boutiques, and multiple breweries. The rental is perfect for business travelers, couples, and solo travelers. It comes complete with one bedroom, one bathroom, a dedicated workspace, a living room, a kitchen, and a screened porch. This accommodation is set on the second floor and you also get a private entrance. Guests also get access to sit in the shared yard that belongs to the hosts.

Stayed at this property?
Chicago, Illinois, United States

13.91 km (8.7 mi) from Ping Tom Memorial Park
356 reviews   Superhost Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
host is very kind
host was friendly and prompt
she was a kind and welcoming host and gave us some great recommendations
our hosts were also incredibly nice and helpful
she was a wonderful host we had everything we needed and more
Location:
great location a short walk to everything
location is very good
great neighborhood convenient location fun vibe
great location easy to walk to restaurants and shops
great location peaceful and quiet
Cleanliness:
clean and had everything we needed
betsy's place is clean and cozy
the house is very clean and homey-feeling
the apartment was beautifully furnished and clean and super comfortable
the bed was super comfortable shower pressure great very clean and nice 3 season porch
Amenities & Room:
amenities allow for coffee and continental breakfast in a roomy apartment great for one or couple
the apartment has amazing amenities and is so thoughtfully decorated
the bathroom (with hot water) was good
charming and cozy with a great enclosed porch
the bed was very comfortable and we had everything we needed
Read more reviews
Monthly discount: 40% off

7. Handicap-accessible home for five (from USD 79)

Situated in a quiet neighborhood, just 12.5 miles (20 km) from downtown Chicago, this two-bedroom home is ideal for up to 5 guests. It’s styled simply and comfortably with two queen-size beds. Guests can chill in the living room while watching TV. The rental features free wifi, free parking, and a dedicated workspace that’s perfect for business travelers and other travelers who are planning to drive around.

Stayed at this property?
Chicago, Illinois, United States

23.62 km (14.7 mi) from Ping Tom Memorial Park
201 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Host:
richard was a wonderful host
unbelievably friendly and accommodating host
he was a very excellent host
richard was a great host
the host was more than happy to offer his help with navigation or suggestions for restaurants
Location:
best location in this price
safe neighborhood and close to a park
cute little place in a lovely neighborhood
great location and even better value
nice neighborhood close to the train
Cleanliness:
richard has excellent communication and the place was very clean and in a very convenient location
very nice neighborhood everything was clean except the bath tub
the place was clean
the house was sparkling clean
perfect economical and clean
Amenities & Room:
we stayed overnight and had a super comfortable experience
nice basic apartment very comfortable
Read more reviews
Monthly discount: 35% off

8. Spacious suite near the downtown train station

This extended-stay Airbnb rental in Chicago is situated in a beautiful historic neighborhood and allows guests to have a comfortable stay for a long duration. It is a suite that has plenty of amenities, including a spacious bedroom and a bathroom. There’s a well-equipped kitchen with a French door that will take you to the sun deck. Here, you can sit by the garden and enjoy a cup of joe. There’s a public park located just two blocks away from the property, where you can go swimming and play tennis. Beverly Art Center, Lincoln Park Zoo, Willis Tower, and Shedd Aquarium are situated just a few blocks away from the rental.

Stayed at this property?
Chicago, Illinois, United States

19.58 km (12.2 mi) from Ping Tom Memorial Park
163 reviews   Superhost Wifi Available
Entire guest suite 4 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Host:
she was a gracious host
janine was a lovely host
jan was a wonderful host and was available if we had questions or concerns
janine was a great host
janine was a lovely host to our family
Location:
easy walk or bike to train to downtown
the location of the house is in a very nice neighborhood close to everything you might need
great location on south side near western ave
this morgan park apartment - near beverly - was the perfect location for us
jan’s place is so cute and colorful
Cleanliness:
clean relaxing and spacious
it was very clean
the house is clean and comfortable
it was warm clean and cozy
the place was super clean and fresh
Amenities & Room:
the bed is amazingly comfortable
the bed is in a separate space and was comfortable
the cozy couch folds out into a twin sized bed- perfect for a child
the kitchen area is well appointed with a lot of natural light
a very comfortable bed and beautifully decorated space with a lovely garden yard and balcony
Read more reviews

9. Remodeled designer home in the heart of Lincoln Square (from USD 49)

Located in the heart of Lincoln Square, Chicago, this renovated apartment is a perfect base for those looking for easy access to explore the attractions of Chicago. The remodeled version of the apartment features marble worktops, the 1920s exposed brickwork, and wooden floors. Guests can also enjoy views of the courtyard as they kick back and sip on a cup of coffee. Willis Tower, Millennium Park, and Shedd Aquarium are just a few of the many attractions near this property.

Stayed at this property?
Chicago, Illinois, United States

12.87 km (8.0 mi) from Ping Tom Memorial Park
353 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
amy was an excellent host
amy is a great host very accommodating and responsive
amy was a courteous and generous host
also amy was very responsive to my questions and replied quickly
communication with host is spot on check in/out is efficient
Location:
great location on lincoln square
great location and convenient to everything in walking distance
the location was great
amazing location great comfortable space
great place in a great location
Cleanliness:
amy’s place was very clean and comfortable
everything was very clean/spotless up to date beautifully decorated
the place is wonderful clean and new
great place clean roomy and very comfortable
amy's place was sparkling clean tastefully appointed and super comfortable
Amenities & Room:
the bed is a full so for couples that cuddle in their sleep it’s great
fantastic location authentic chi building quiet and comfortable
beautiful apartment in beautiful and fun street
Read more reviews
Monthly discount: 25% off

10. Bright and airy townhouse near University of Chicago

Set across the street from the University of Chicago campus, this bright and airy, three-bedroom townhouse has an open-concept space with a fully furnished living room, dining area, and a kitchen. Along with this, on the lower floor, guests get access to the bathroom and a separate room. There’s also a private porch and an attached private garage. Guests get easy access to the parks, beaches, museums, and lakes, and also to the bus and train station.

Stayed at this property?
Chicago, Illinois, United States

8.54 km (5.4 mi) from Ping Tom Memorial Park
67 reviews  
Entire townhouse 3 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Host:
host was extremely responsive
isabel was a great host
the owners were also very responsive and communicative
had a great time and host was responsive and available
the host was very understanding and helpful to mention each and everything
Location:
great location quite neighborhood located by the university of chicago
terrific location while visiting uchicago
we found that all interest points are close near chicago university
great location for visiting university of chicago or hyde park area
excellent location loved walking to university of chicago and local areas
Cleanliness:
clean with nice decor
very clean and lots of space
the house is super clean and comfortable
everything was very clean and comfortable and the kitchen was well stocked
the neighbourhood feels clean and safe
Amenities & Room:
the beds were especially comfortable
we felt comfortable and safe
Read more reviews

Explore the beauty of Chicago

Chicago has plenty of places that can offer travelers a fun-filled experience. From perusing museums to going on a hike, exploring the zoos, parks, gardens, and several other attractions, Chicago has something for everyone. If you’re planning to stay for long here, you can refer to this list of the best Airbnb monthly rentals in Chicago, Illinois.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Born in Mumbai and brought up in Bangalore, India, Aarti is a full-time freelance writer by profession. She is a lover of everything the ‘blue dot’ offers—world cultures, off-the-beaten tracks,...Read more

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