
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.
Chicago, Illinois, United States
10.22 km (6.4 mi) from Ping Tom Memorial ParkSuperhost
Accommodates: 6
Top guest reviews
Host:
they were the perfect hosthosts were super responsivehosts were responsive and kind toohosts were readily available and kindshe was understanding and kindLocation:
it is located in a great neighbourhoodnice location and nice placegreat location beautiful comfy spacealso very close to some wonderful mexican restaurants that deliver late nightit was reasonable and close to some cool venuesCleanliness:
clean and comfortable stayclean and nicely decorated housewas very clean and homeyeverything was truly clean and comfortableclean chic and comfyRead more reviewsAmenities & Room:
smart tv was complete with sling netflix amazon etcbeds and bedding were perfectvisited during winter but the heater was very nice and kept us both warmbed were super comfortablepaige and nathan's main floor apartment was perfect for our visit to chicago
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.
Top guest reviews
Host:
she is a very good hostthis place was lovely and the host just as kindaudra was an amazing host she was very hospitable and prompt responseif you're sensitive to noise you can definitely hear everything above you since the host lives therean amazing host will definitely stay there againLocation:
i enjoyed the neighborhood so close to everythingsuper spacious place near lots of restaurantsthe location is close to public transit and a hop-skip away from chicago's major attractionswe were within walking distance of great restaurants and barsthere’s also good places to eat within walking distance and it’s so close to downtownCleanliness:
the space was clean and cozyvery clean stylish and comfortablegreat modern space very clean and comfortablethe interior is very clean and modernvery clean well-appointed apartment in a terrific neighborhoodRead more reviewsAmenities & Room:
enjoyed the nice little patio and cool a/cthis is a very nice apartment with all the necessary appliances and spaces for a pleasant staythis place is great i'm pretty picky about beds and i thought the mattress was comfythe kitchen is so well equipped which makes cooking for yourselves easy if you want tothe space was beautiful and comfortableMonthly 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.
Top guest reviews
Host:
very responsive hostvery thoughtful host who went the extra milevery nice and convenient flat with a careful owner that answers very quickly and is very helpful when requestedpuppy quite friendly that lives upstairsluke is a great host and checked into make sure we had everything we neededLocation:
great location for visiting u chicagogreat location in hyde park a few blocks from campusthe location was fantastic and luke was thoughtful in offering snacks for usvery close to the jewel grocery storelocation location location great for uc campus access and provisions/restaurants nearbyCleanliness:
clean comfortable placeit was so clean and cozyplenty of clean towels and extra blanketsthe apartment is clean and convenientthis condominium was very clean and comfortableRead more reviewsAmenities & Room:
we had room to spread out and relaxwe had everything we needed for our stay plenty of linen and comfortable bedswonderful welcoming super clean and larger than expected apartment literally across the street from uchicago's south campus residence hallthe apartment is big with plenty of space to relaxwifi worked perfectly and all the info we needed was readily availableMonthly 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.
Top guest reviews
Host:
jb is a great host and is prompt with responsesjb was a wonderful host absolutely gorgeous spacejb is a wonderful host (and a talented artist himself)jb is a very pleasant hostjb was an excellent host very attentive and communicative - everything went very smoothlyLocation:
great place in a cute neighborhoodbeautiful unique location in historic pullmanalso super close to the train to go downtownthe location is terrific with convenient access to the metragreat quiet location in a wonderfully historic apartmentCleanliness:
its a clean clean clean placethe bed was clean and comfortablereally unique and clean space in a historic neighborhoodthe neighbors were all very friendly and the apartment was clean and comfortablethis place was fantastic to stay at very unique clean and quietRead more reviewsAmenities & Room:
cozy house with really cool decor and great amenitieswas worried at sight of small double bed but the comfort had me sleeping like a babyit was nice to have a full working kitchen to save money on mealsjb’s apartment was absolutely perfectthe beds were comfortable and everything was in great shape for our visitMonthly 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.
Top guest reviews
Host:
host was very friendly and helpfulthe host was very professional amd friendlyfortino was such a great host timely responses so helpful when answering our questionsgreat host will definitely be booking againamazing stay host is great and fast responseLocation:
i liked the locationgood place for stay good location everything is nearperfect location close to the airport and nice and cozythe place was really nice and the location was near to the metro stationvery convenient location near the city and great restaurantsCleanliness:
clean and quick on respondingplace was very clean parking was better than expectedi was very clean he gave us a lot of location tips and the communication was goodplace is super comfy and cleansuper clean and comfortable apartment was actually sad to leave it because it felt so cozy i loved itRead more reviewsAmenities & Room:
comfortable bed nice shower spacious closet spacefortino’s place was comfortable and had everything we neededhe was super responsive to my messages and provided a lot of details that helped my stay comfortableMonthly 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.
Top guest reviews
Host:
host is very kindhost was friendly and promptshe was a kind and welcoming host and gave us some great recommendationsour hosts were also incredibly nice and helpfulshe was a wonderful host we had everything we needed and moreLocation:
great location a short walk to everythinglocation is very goodgreat neighborhood convenient location fun vibegreat location easy to walk to restaurants and shopsgreat location peaceful and quietCleanliness:
clean and had everything we neededbetsy's place is clean and cozythe house is very clean and homey-feelingthe apartment was beautifully furnished and clean and super comfortablethe bed was super comfortable shower pressure great very clean and nice 3 season porchRead more reviewsAmenities & Room:
amenities allow for coffee and continental breakfast in a roomy apartment great for one or couplethe apartment has amazing amenities and is so thoughtfully decoratedthe bathroom (with hot water) was goodcharming and cozy with a great enclosed porchthe bed was very comfortable and we had everything we neededMonthly 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.
Top guest reviews
Host:
richard was a wonderful hostunbelievably friendly and accommodating hosthe was a very excellent hostrichard was a great hostthe host was more than happy to offer his help with navigation or suggestions for restaurantsLocation:
best location in this pricesafe neighborhood and close to a parkcute little place in a lovely neighborhoodgreat location and even better valuenice neighborhood close to the trainCleanliness:
richard has excellent communication and the place was very clean and in a very convenient locationvery nice neighborhood everything was clean except the bath tubthe place was cleanthe house was sparkling cleanperfect economical and cleanRead more reviewsAmenities & Room:
we stayed overnight and had a super comfortable experiencenice basic apartment very comfortableMonthly 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.
Chicago, Illinois, United States
19.58 km (12.2 mi) from Ping Tom Memorial ParkSuperhost
Accommodates: 4
Top guest reviews
Host:
she was a gracious hostjanine was a lovely hostjan was a wonderful host and was available if we had questions or concernsjanine was a great hostjanine was a lovely host to our familyLocation:
easy walk or bike to train to downtownthe location of the house is in a very nice neighborhood close to everything you might needgreat location on south side near western avethis morgan park apartment - near beverly - was the perfect location for usjan’s place is so cute and colorfulCleanliness:
clean relaxing and spaciousit was very cleanthe house is clean and comfortableit was warm clean and cozythe place was super clean and freshRead more reviewsAmenities & Room:
the bed is amazingly comfortablethe bed is in a separate space and was comfortablethe cozy couch folds out into a twin sized bed- perfect for a childthe kitchen area is well appointed with a lot of natural lighta very comfortable bed and beautifully decorated space with a lovely garden yard and balcony
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.
Top guest reviews
Host:
amy was an excellent hostamy is a great host very accommodating and responsiveamy was a courteous and generous hostalso amy was very responsive to my questions and replied quicklycommunication with host is spot on check in/out is efficientLocation:
great location on lincoln squaregreat location and convenient to everything in walking distancethe location was greatamazing location great comfortable spacegreat place in a great locationCleanliness:
amy’s place was very clean and comfortableeverything was very clean/spotless up to date beautifully decoratedthe place is wonderful clean and newgreat place clean roomy and very comfortableamy's place was sparkling clean tastefully appointed and super comfortableRead more reviewsAmenities & Room:
the bed is a full so for couples that cuddle in their sleep it’s greatfantastic location authentic chi building quiet and comfortablebeautiful apartment in beautiful and fun streetMonthly 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.
Chicago, Illinois, United States
8.54 km (5.4 mi) from Ping Tom Memorial ParkTop guest reviews
Host:
host was extremely responsiveisabel was a great hostthe owners were also very responsive and communicativehad a great time and host was responsive and availablethe host was very understanding and helpful to mention each and everythingLocation:
great location quite neighborhood located by the university of chicagoterrific location while visiting uchicagowe found that all interest points are close near chicago universitygreat location for visiting university of chicago or hyde park areaexcellent location loved walking to university of chicago and local areasRead more reviewsCleanliness:
clean with nice decorvery clean and lots of spacethe house is super clean and comfortableeverything was very clean and comfortable and the kitchen was well stockedthe neighbourhood feels clean and safe
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.
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