10 Best Airbnb Vacation Rentals In Downtown Chicago, Illinois - Updated 2022


Whether you are travelling to see parks, national landmarks, museums or just craving to have a night out with a view of an amazing skyline, Chicago in Illinois is the place for you! With its beautiful landscape and scenic lakeshores, you won’t be lost. Chicago is home to many towering skyscrapers and friendly people. It even has hundreds of hotel properties and ample accommodation for a restful vacation. This third-largest city in the U.S. is proud of its diverse culture, making it very friendly to tourists and visitors alike. This place has a lot to offer to people of all ages, so whether it’s a family vacation or you’re going solo, here are some of the best Airbnb in downtown Chicago, Illinois.

1. Luxurious sky home in the heart of downtown (from USD 345)

Check out this pad if you’re looking for a centrally located accommodation in downtown Chicago. It can sleep up to six people in total comfort thanks to its two large, fully furnished bedrooms. The living area, dining area, and kitchen have floor-to-ceiling windows that offer a panoramic view of the city. The modern condo is conveniently located within the downtown area, offering easy access to the Navy Pier, Magnificent Mile, Millennium Park, shops, restaurants, cafes, bars, and other establishments.

Lux Sky Home near Navy Pier and the Magnificent Mile
Chicago, Illinois, United States
29 reviews Superhost  Wifi Available
Entire condo 2 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
amazing views of the city great location close to everything and great amenities in the building (gym pool etc)
the apartment is gorgeous with great views clean and spotless and the hosts were extremely welcoming and responsive
everything was great the host was very responsive
the host was very communicative and made for a peaceful and enjoyable stay
the hosts are super responsive and interested in you having a great stay
honest and so easy to deal with rudy was so helpful and knowledgeable
he was extremely courteous and responsive
great location and a great space
the best location you can find in downtown chicago
the location couldn’t get any better just steps away from michigan ave
this unit was amazing the location was perfect
great place to stay for long term
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2. Modern and sleek private home

You will surely love this apartment because of its industrial look, minimal design with a lot of space. With one bedroom and a bathroom, this place is suitable for couples or small families. The building also has accessible amenities such as a fitness center and a pool. This spot was featured in travel magazines too. You can never go wrong with this place because it has everything you need – from comfortable beds, fantastic view of the city and accessibility. It has everything to make your vacation a memorable one.

Great locationDowntown Apartment Nice View monthly
Chicago, Illinois, United States
175 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the views from the apartment are great
great view very comfortable highly recommended
the view is superb and the apartment has everything you need
the city view from the apartment window at both day and night are amazing
the space is very comfortable
very clean and comfortable apartment
clean cozy convenient communication was on point
the space was clean cozy and relaxing
the space is very modern stylish clean and comfortable
only complaint-- a man insisted on coming inside to clean 10 minutes before check-out time
host was extremely responsive
jing was very accommodating and courteous
very accommodating and welcoming host
jing answered all our questions within minutes and was very helpful with storing our luggage on checkout day
jing was a fantastic host with some really thoughtful touches
the location was great
great location within easy walking distance to downtown or the train station
nice location in a safe building
train to/from airport is an easy 8 minute walk
great apartment and the location is close to everything
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3. Perfect resting spot for busy professionals

This is just a perfect resting or staying-in spot in Chicago. This place really holds to its value. It’s clean, cozy and near all the Chicago landmarks and hotspots. It can also be the perfect place for work trips. It’s quiet and is equipped with comfortable furniture when you are working on your laptop. Wake up and go home to this spacious and pleasant apartment located at the center of the city. Have your peace of mind while working or on vacation while staying here. Don’t forget to peek out to get an excellent view of Chicago by night.

Beautiful Spacious 1BR in Downtown With Super host
Chicago, Illinois, United States
234 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom

4. Stylish apartment in a safe neighborhood

Be at home in this safe neighborhood, it’s perfect to get that whole Chicago living experience. This may not have breath-taking views as the others but to live in Chicago’s West Loop neighborhood can be a whole new experience. Close to transport hubs and famous spots, this place is suitable as a starting point for your Chicago exploration. A simple one bedroom one bathroom apartment with a kitchen, this place is for you if you are in for a legitimate city-living weekend or vacation. Whether you want to eat out, go shopping, have a night out or just simply stroll at the park, this place is only minutes away from all the attractions.

Great location Stylish Downtown Apartment 5
Chicago, Illinois, United States
222 reviews
Entire apartment 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
full of amenities smart tv blue ray players coffee machines kitchenwares you name it
good bed and good ac
the wifi was pretty fast and the snacks provided were a nice touch
it has everything you need a king bed clean sheets heating a room finely finished and decorated
the space itself was thoughtfully laid out with a spacious living room and full kitchen
clean and very comfortable
the place was immaculately clean
great spot was clean and cozy
very clean building with friendly and quiet neighbors
very clean comfortable sleeping arrangements
jing is a great host
jing was very responsive with any questions or concerns
very kind and thoughtful host
jing was very responsive and helpful
really good comms from our hosts and they were very helpful throughout our stay
great location close to everything
its location its good
great location and security system
close to the train station and a bunch of good restaurants
great location would definitely stay again
Read more reviews

5. Peaceful spot for a quiet me-time

Overlooking the city, you can find peace and solitude in this 46-story high apartment. It is the perfect place if you want to be alone. And if you have decided to go out and explore the city, everything is just at a walking distance including bars, restaurants, stores, and parks. The place is also perfect for families. It is comfortable and complete with kitchen amenities. So whether you’re staying in or going outdoors, you are sure to enjoy your stay. You’d want to make this your home whenever you’re in Chicago.

Cozy 1br by Milllennium Park
Chicago, Illinois, United States
352 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the wifi wasn’t the best so if traveling on business it’s good to know
loved the workout room upstairs the location and the views
apartment is clean and spacious
the rooms were clean & stocked with towels
great position clean and confortable
the apartment is extremely clean and they are very responsive
the place is really clean
hosts are very quick with responses and helpful
hosts communicated well and were very responsive to my questions
great hosts that are responsive and welcoming
the host was very helpful with my checking in
the hosts are nice and very responsive
close to lots of great shopping and millennium park
the location was very good
really great location for visiting chicago
great location great rental space
great location will stay again
Read more reviews

6. Chic studio apartment in the heart of downtown

Experience Chicago in style and stay in this chic accommodation in the heart of downtown. It can accommodate up to two guests, great for solo travelers and couples. It comes with one cozy queen bed, a bath, a sitting area, a dining area, and a full kitchen—all fully equipped and furnished for your comfort and convenience. Amenities include high-speed WiFi, perfect if you’re on a workation. Its convenient location means you will have quick access to many leisure and business spots.

Sonder | Jewelers Row | Studio Apartment
Chicago, Illinois, United States
147 reviews  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the apartment comes with a washer/dryer and included detergent which was very helpful for us
the small studio apartment was the perfect size for the two of us
we had an overall good stay at this apartment
the actual apartment was really nice as well
bed was definitely on the firm side but would recommend to anyone
very clean room and is as advertised
clean apartment with everything you need
apartment was really clean and well-stocked
the space was clean and had all necessities
the interior of the studio apartment was clean and modern
great location super cozy room
the location was perfect near the art institute goddess and the baker cafe millennium park
about the only positive is that the location is close to public transport
great place and great location
great location near millennium park the river walk and michigan avenue
Read more reviews

7. Studio with a mix of simplicity and convenience

Another place if you are looking for that breath-taking view of the city. Located on the 42nd floor of a luxury building in the heart of Chicago, it is the perfect spot for just sitting, sipping coffee or wine and just taking in the Chicago view. It is a simply designed one-bedroom apartment equipped with everything you need. Whether it’s a work trip or vacation, this apartment is conveniently located for all you need and want to do. Safe, comfortable and convenient.

Sonder at Grant Park | Superior Studio Apartment w/ Lake View
Chicago, Illinois, United States
335 reviews  Wifi Available
Entire rental unit 2 Beds 4 Guests 0 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
beautiful rooms and great view of city
small but stunning view of lake michigan and infinity pool in master bedroom
definitely take a dip in the pool
wonderful apartment view of the lake location
the view was beautiful kitchen was well stocked and the location was fantastic
very clean and convenient apartment
clean new modern building
the apartment was very clean and modern
the apartment was sparkling clean
amazing place very clean will stay again
the host was extremely responsive
all the staff were super friendly and helpful
the staff for sonders and essex were both super responsive and very helpful
sonder on site staff were very helpful
the location was great
great location its close to everything
absolutely fantastic location right across from grant park
great location and cute room
definitely recommend location is great
Read more reviews

8. White and squeaky clean dwelling

This apartment is the perfect place to go home to after partying or sight-seeing. With its clean, almost all-white design, it is sure to make you feel relaxed after a long day. This place is worthy of good feedback for its cleanliness, security, and efficiency. Another place in the center of the city where almost everything is nearby, you can never get lost. It has two beds, one bathroom, and a kitchen. Be sure to bookmark this place for future accommodation.

Sonder at Grant Park | Spacious One-Bedroom Apartment w/ City View
Chicago, Illinois, United States
156 reviews  Wifi Available
Entire rental unit 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the apartment had a great view and was fully stocked
cons:the mattress on the sofa-bed can be improved
the kitchen and living room is stylish and the coffee and tea were a nice touch
this apartment was everything perfect space with big bed and a pull out couch
the king bed was super comfortable and my girlfriend and i both slept deeply through the night
super clean and spacious
super clean stylish and the communication was outstanding
super clean and decorated so cute
it was a nice modern and clean places to stay
it was extremely clean stylish yet comforting
the staff were above helpful with questions
once the host responded we had much better communication and they apologized for the delayed responses
the customer service was top not and the sonder team was very responsive
the sonder was easy to access and the people in the office were helpful knowledgeable and welcoming
amazing location close to everything we wanted to do
great space great location
it was in the perfect location and close to everything we wanted to do downtown
great location & loved the security
excellent space in a convenient location
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9. Sophisticated apartment with a great view

This cozy and sophisticated one-bedroom one-bathroom apartment is in one of the best and safest locations in Chicago. This place is located in the heart of the city, placing you above the clouds for it is on the top floor of a high-rise building located close to many hot spots, bars, and restaurants. Not to mention the friendly hosts and a lot of building amenities. The indoor pool, hot tub, and sauna are just a few of the offerings you can access during your stay.

LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Chicago, Illinois, United States
285 reviews
Entire apartment 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
beautiful view and amazing apartment
very comfortable bed & couch ( if you like softer beds)
the views from the living room/bedroom are amazing
the view is stunning great location and the bed (and couch) are super comfortable
the apartment is nice and the view is good
the apartment is very clean
well appointed and very clean
the apartmentwas very clean and felt like home
would absolutely stay here again clean
the bed was very comfortable and everything was very neat and clean
hosts had quick response time and were extremely helpful when needed
host was informative and easy to contact
they were very friendly responsive hosts and made sure all expectations were clear and questions were answered
margarita and mike were super responsive before and during our stay when we had questions
margarita was very accommodating and helpful
great location for our trip to town
great location and stylish space
amazing place in amazing location
the location was super convenient
very neat place with great location
Read more reviews

10. Gorgeous penthouse with private rooftop

This huge space in the heart of the city really shouts chillin’ in Chicago. This modern loft is suitable for hosting small parties because it can fit up to 10 guests in its 2 bedrooms, 2 bathrooms, and a spacious common area. The vibrant design of the apartment will make you want to stay in and just enjoy the place. The rooftop is perfect for viewing the city skyline. You can also take a quick stroll to nearby establishments. The modern and cozy feel of this place is perfect for winding down from the hustle and bustle of city life.

Downtown Penthouse with Private Rooftop!
Chicago, Illinois, United States
103 reviews
Entire apartment 5 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
nice modern apartment with all the amenities
it might be beneficial to provide an additional deluxe air mattress so sleeping 10 would be more comfortable
huge living space and kitchen
would have liked a/c to be a little colder
the beds were super comfortable and the decor super chic
the unit was very clean
the space was very clean and exactly what was presented
nice clean place on inside of penthouse
perfect loved the place & it was impeccably clean and awesome deal
place was very clean and spacious perfect for a big group
despite us checking in late the host was helpful and accommodating
he was super friendly and a wonderful host highly recommend staying here
everyone in the building is friendly and the host (dan) gave some terrific recommendations
dan was a great host and the apartment was super easy to check in and out
dan is an excellent host
great place great location
good value close to downtown
nice place in a great location
beautiful place great location
beautiful place in an excellent location
Read more reviews

Visit Chicago's favorite neighborhood

This city attracts millions of visitors each year because of its rising tourism, attractions, and many business opportunities. Dwellings and locations for rental have also surged because of the demand. There are many spots to choose from in Chicago whether you’re looking for a place with historic architecture or stunning rooftops.

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

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Maui Hermitanio is a Manila-based content writer. She is most interested in writing about international cuisines, popular food stops, and destinations with beaches and outdoor sceneries. She has...Read more

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