Top 10 Short Term Rentals In Chicago, Illinois - Updated 2022


Chicago, Illinois, is perhaps one of the most famous cities in the United States. According to statistics, it is also the third most populous city in America. It’s no wonder why people are flocking to the “windy city”. It is a world-renowned hub for finance, culture, transport, and commerce. The city has a booming economy — do you know that the city alone has one of the highest gross domestic products (GDP) in the world? Besides a booming economy, Chicago is also home to a diverse cultural scene. Art buffs can talk for hours about the city’s numerous public installation, while music lovers have a wide genre to dive into. The city’s unforgettable attractions include the Willis Tower and the ever-famous Chicago River. Scroll down for the top 10 short term rentals in Chicago, Illinois.

1. Modest top-floor apartment in a residential area (from USD 105)

Looking for a simple place to crash? This modest top-floor apartment is your best bet, especially if you’re tagging along with some friends or bringing the whole family along. This unit is located in a residential area, so you can enjoy your peace while in the city. All the amenities you can ask for are here. The living room has a plush sofa with a fold-out bed and cable TV. The bedroom seems cramped, but it is actually spacious for two, all thanks to the queen-size bed. The spacious, well-stocked kitchen is located at the entrance. This unit also comes with a backyard and a garden area. When it’s time to explore, make sure to check out the chic bars and award-winning restaurants within the neighborhood.

Logan Square Lookout
Chicago, Illinois, United States
361 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
shower amenities and some extras were provided like coffee tea shampoo etc
i just wish i could have had a space heater to make it cozy during the winter
very accurate description of the apartment walkable to public transit neighborhood feels very friendly
the space was nice and quiet and very comfortable
i like the large kitchen however the bedroom and bathroom are really tight
it was clean and had plenty of space
the apartment was clean and nice
clean simple place very communicative
the place was so clean and private
the apartment was very clean and the neighborhood felt extremely safe
hosts were very nice
very responsive host
we enjoyed our stay and thought the host was very communicative
patrick was a very responsive & helpful host
super friendly and accommodating hosts
location was great
great location and very adequate accommodations
the location is in a great spot
this is a great location
nice place in a good location
Read more reviews
Weekly discount: 10% off

2. Airy and minimalistic apartment with backyard (from USD 70)

Host Marissa invites you to stay at her Airbnb rental located in the basement of her family’s abode. The entire apartment is well-ventilated and has a simple design that gives off a spacious and minimalistic vibe. Only two can fit comfortably inside though. You and your companion will have a queen-size bed all to yourselves. You’re also welcome to enjoy a varied selection of award-winning movies and Netflix shows from the comfort of the living room. You can cook a meal or two in the kitchen; however, the oven is not really functional at the moment. Still, it’s better than nothing, and what you’re getting here is a bargain, especially when you consider the fact that it is minutes away from great hangout spots and downtown Chicago.

Spacious in-law Apt: 15 min to O'Hare and Downtown
Chicago, Illinois, United States
176 reviews Superhost  Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the house was super cozy and had everything we needed in it
the place was cute and clean they had coffee water beer for us and even some breakfast bars
our stay was very comfortable and would definitely stay again if we come back to chi
nicely maintained and clean space
clean stylish and fun
this place was so clean the bed was extremely comfortable
their place was sparkling clean and cozy as well
the place is very clean and well maintained
the host is attentive and provided good local knowledge
best hosts yet both hosts were super welcoming and helpful
hosts were quick to respond and were there to help
great little place hosts were super considerate
nathan was very helpful with his recommendations as well
great location near the airport
good location with easy parking
i'm so glad i chose this location
super close to the bus stop which made everything easier
the place is located in a very nice neighborhood with access to many restaurants stores etc
Read more reviews
Weekly discount: 10% off

3. Contemporary unit with a rustic feel (from USD 114)

If the sixth listing is already booked, then choose this instead — a modern, contemporary apartment with a rustic feel. It’s unmistakably rustic, thanks to the warm tones and dark hues prevalent in the furnishings and decor. Twin bedrooms offer respite to weary travelers, with a comfy mattress on the queen-size and double-size beds, thus providing a good night’s sleep. The sofa in the living room is large enough for a single person. Speaking of entertainment, you and your companion can bond over movies and shows as the property features internet-connected smart TV. Better yet, bond over with your friends or family as you cook the most delicious meals in the kitchen. The bonding doesn’t have to stop there since downtown Chicago is just a ride away.

Large On Space, Huge On Comfort
Chicago, Illinois, United States
120 reviews  Wifi Available
Entire rental unit 2 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the apartment is spacious and beautiful with necessary amenities for making meals as well as relaxing
it was a special treat that it had 2 bathrooms
the apartment was as described and is a great value for chicago
beds were comfortable
nice clean and really spacious
looks just like the pictures; very clean; very spacious
the house was really nice and clean
the place was clean smelled great had street parking and looked as pictured
very clean and a lot of space which made our stay comfortable
jay was a wonderful host
jay was a great host
thank you jay for hosting
the host communicated very well and was willing to answer any questions i may have had
he dropped off brand new pillows and cases when requested which was very kind
we were in a perfect location in chicago
we were 15 min away from our conference and we enjoyed being close to everything down town
a great place in a great location for a great price
the neighborhood was great it was quite and close to everything
location - residential safe and quiet
Read more reviews
Weekly discount: 10% off

4. Newly renovated unit with minimalist decor (from USD 92)

This Airbnb unit was recently renovated to fit the sensibilities of modern times. Inside, the furnishings and the decor are kept to a bare minimum. You could very well say that it adheres to a minimalist design. The unit is designed for couples with its single queen-size bed, but it could fit one person more, thanks to the lofty sofa in the living room. Working on the go has never been easier, thanks to WiFi access and laptop-friendly workspaces. Meanwhile, preparing a meal is a breeze here as the unit has an organized and well-stocked kitchen. Transportation access is not a problem because the unit is close to the Jefferson Transit Center.

❤️The Perfect In Between❤️
Chicago, Illinois, United States
161 reviews  Wifi Available
Entire rental unit 2 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the place had great amenities and it was nice that there was a full kitchen
the place has a touch of modern and a nice kitchen with amenities
the place is small & super cozy
we had an amazing and comfortable stay and i would definitely book with them again
in addition he had some great amenities and all of the kitchen appliances that you could need
everything was clean nice and comfortable
very clean and had everything we needed
this was such a clean nice space
the apartment was clean and included everything we needed
mark's place was amazing it was clean spacious and quiet
quick responses and super nice host
they were super quick with their responses and were very accommodating
i received quick responses whenever i needed anything and the hosts were very helpful
thank you for hosting us
mark was a great host who responded quickly
great location and amazing stay
great location for a great price
great location and convenient parking
this apartment is small but cute great location
the location was very nice and quiet
Read more reviews
Weekly discount: 10% off

5. Romantic studio located near Gold Coast (from USD 102)

Couples scouring for a two-person studio have this place to call home away from home. It’s a simple studio located near the Gold Coast, but its proximity to Oak Beach and Magnificent Mile means that it is very near to some fantastic spots in the city. The studio has everything that you and your partner can ask for. It has a laptop-friendly desk, a cable TV plus WiFi access for catching up on important matters. The cushy mattress of the queen-size bed offers a well-deserved rest for the night. The kitchen is well-stocked, too. You don’t have to worry about forgetting your towels at home since linens are generously provided by the host.

Great Location Studio in the Gold Coast!!
Chicago, Illinois, United States
249 reviews Superhost  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
small bathroom large closet great wifi and comfortable bed
comfortable bed and good amenities
the apartment is small but was perfect for us on our long weekend trip
amazingly clean and cozy
very clean and terrific communication from the host
the place was very clean
space is clean and we had everything we needed
the room itself was very clean and perfect for a short trip
great host and thank you
host was extremely responsive and patient with all my questions
dino was a great host
dino was very responsive to any questions we had
the host was great and quick to respond
great location for a quick trip to chicago
this location really is great
very convenient location and comfortable place
great central location and easy access to cta
great location if on a budget
Read more reviews
Weekly discount: 10% off

6. Quiet studio within Jefferson Park (from USD 97)

This studio is located within the serene Jefferson Park. A few walks from here and you will be at the Blue Line that facilitates easy access to downtown Chicago. This studio is also close to great restaurants and bars, if hanging out is your kind of jam. Since the whole house is shared between tenants, the host will be providing you keys for the bedroom, kitchen, and large closet. It may not look much, but the whole space is comfy and spacious for two people. The studio also comes with free WiFi access, so you can watch Netflix on the TV before calling it a night. The kitchen is fully equipped with utensils and appliances for a delightful meal prep time. Meanwhile, the bathroom has a shower so you can rejuvenate after a tiring day in Chicago.

Comfort & Clean!! 15 min ORD/Dwntwn1 & Parking
Chicago, Illinois, United States
189 reviews  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the photos make the room seem more spacious that advertised bit still had a great time in this place
(oh and pillows / bed are super comfy )
nice place and very conveniently located the wi-fi was pretty much non existent but everything else was great
the mattress was comfortable and the place was clean
clean nicely appointed kitchen
this place was very clean and nice
the apartment is clean and beautiful
the place was clean and offered privacy
very nice and clean small and great for a person or a couple
nora is a very kind host and happy to help us out
well taken care of and great host
thermostat is controlled by owners phone and owner is really responsive about making the temperature comfortable for you
this place is awesome great and friendly host we were welcomed very well
they were also very quick and responsive each time i had a question or a sudden change request
it is located at a good location near to jefferson park
very cute place in a great neighborhood
very cute and modern place located in a nice neighborhood
good location and felt safe
food close by and easy access to rosemont
Read more reviews
Weekly discount: 10% off

7. Well-lit apartment near Montrose Beach

The first in the list is this well-lit apartment East Lakeview with enough space for three people. The apartment unit has a luxurious vibe to it, thanks to the elegant decors. The living room, dining area, and kitchen are all incorporated into one huge space. The open space is cozy enough for an afternoon get-together, thanks to the plush sofa and large flat-screen TV upfront. The bedroom, meanwhile, invites you for an invigorating rest, thanks to a comfy mattress on the queen-size bed. There’s a balcony, as well, perfect if you want a breath of fresh air. On top of it all, this unit is within walking distance to Montrose Beach and Wrigley Field.

Updated Vintage Apt. near Wrigley/ Uptown & Beach
Chicago, Illinois, United States
71 reviews  Wifi Available
Entire rental unit 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
it was really clean and smelled great when we came into the apartment
great area and comfy + clean airbnb
very clean and unique place great neighborhood
jamie and nathan’s place was very clean and well put together
the apartment is clean spacious and totally worth its value
the hosts were always in contact if needed and the building owner was courteous and helpful
our hosts jamie and nathan were incredibly responsive and went the extra mile for us during our stay
hosts were helpful & truly let us see the city from such a great spot
jamie and nathan were terrific hosts and were very easy to communicate with
jaime was very accommodating and friendly
the location was great
well located and efficient space
wonderful location would stay again
super nice place great location
not super close to big tourist attractions but an easy uber/metro ride away
Read more reviews

8. Private and cozy apartment in a quiet neighborhood

Simple, clean, and modest are three words that can aptly describe this apartment. It is the perfect place to cap off a day’s worth of exploring Chicago since you’ll be staying in a quiet, residential neighborhood. The double-size bed in the bedroom and a twin-size bed in the living room provides respite for three guests. The open-space living room and the kitchen are spacious enough and kept to a bare minimum. Thanks to the WiFi access, TV, and coffee maker, you can catch up on the latest updates while enjoying your daily cup of joe. Towels and linens are provided for, and there’s a coin-operated laundry, if you rigorously wash your clothes. On top of it all, it’s close to fantastic bars and mouth-watering restaurants.

Cute and cozy one bedroom near trains and airport
Chicago, Illinois, United States
124 reviews
Entire apartment 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
there was tea and coffee provided and the shower had great hot water and water pressure
very clean and convenient
maggie’s place was clean and cozy
very clean private little space
maggie's place was exceptionally clean and comfortable
the space is clean and comfortable
the host was great with fast responses
host was responsive and very helpful
everything was perfect 5* host & apartment
lovely place great host would recommend again
the hosts kept to themselves but responded in a timely manner which was perfect
nice location and cozy place
it's a cute basement place
great airbnb great location great price
maggie’s place is cute and cosy in a good location and in a safe neighbourhood
nice quiet apartment close to o’hare and i-90
Read more reviews

9. Contemporary rental located in Old Town

There’s nothing old with this contemporary apartment located in the Old Town district. The decor and furnishings are well-thought-out. The design of the apartment will suit any sensibilities as it features cool, retro hues that blend well with warm tones of the wooden flooring. The open space concept means that you have all the space to relax anywhere you want. Two guests can comfortably sleep on the queen-size bed, with the large TV providing occasional entertainment. In the morning, have an energizing cup of coffee with the help of the K-cup coffee machine. The unit’s balcony provides a space where you can enjoy the view and reflect on life in general.

S5 Old Town / Downtown / Lincoln Park / Gold Coast
Chicago, Illinois, United States
135 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
the place was clean and comfortable
was great with communication and the space was so clean
clean affordable and easy check in
very clean place for a great price
squeaky clean and good communication
she was a great host and was easy to communicate with
great place & great hosts
tj was an excellent host
host is very helpful and responds quickly
otherwise the apartment was great and the host was a quick communicator
cute apartment in a great location right in old town
great location and prime apt
the location is perfect right in old town and very close to all the museums
great place location and value
stylish apartment in a great location and great value
Read more reviews

10. Vibrant house with a vintage vibe

If you’re looking for a house with a space for a group of five, then look no further. This house is open for travelers looking to maximize their budget while traveling in Chicago. The furnishings and decor give off a vintage vibe to the whole house. On top of it all, it is very spacious for a house located in the city. Travelers who like to hit the road may park their car inside — it’s free and space is part of the house. The living room is well-lit and has large windows to let sunlight in. At night, you and your companions may stay in either one of the two bedrooms that have a queen-size bed, and double and single-size beds respectively. Nearby tourist spots include Frank Lloyd Wright’s home and studio as well as The Humboldt Park.

232 reviews  Wifi Available
Entire residential home 3 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
comfortable rooms and amenities
wifi tv netflix extra blankets and cool books
the tv is easy to use wifi is included and you have free parking
couldn't have asked for a better experience oh and the beds were very comfy
luis’s house is a good size with a lovely relaxing lounge and a fully functioning kitchen
the unit was very clean and comfortable
clean and roomy place to stay
a clean and spacious home
clean tidy and very relaxing space
super clean nice place i would highly recommend
he was a great host
the host was very nice and polite
great price and a great host
luis the host is very accommodating and goes the extra mile to help with advice and guidance
great stay and host
good location near public transit
easy access to city by bus and train
the location is pretty quiet and felt safe
if you know your way around the city with the public transportation really good place to book
the location is about 20-30 minutes from most chicago landmarks we used uber which worked out great
Read more reviews

Explore the Windy City

Chicago is truly a city that you must not miss because of its diverse culture, a booming economy, and top-notch attractions. So, why not come down to the windy city and enjoy what it has to offer to travelers? One only needs to choose from the varied selection of Airbnb rentals to get started.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Kenrick Buduan loves writing. He writes about various stuff, focusing mostly on analysis of society and technology. He contributes to various news platforms too. As a writer, he yearns to travel...Read more

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