10 Best Airbnb Vacation Rentals In Downtown Chicago, Illinois - Updated 2021

airbnb in downtown chicago
Maui
Maui
Updated

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. Studio with a mix of simplicity and convenience (from USD 296)

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
264 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
Cleanliness:
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
Host:
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
Location:
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

2. White and squeaky clean dwelling (from USD 313)

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
153 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
Cleanliness:
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
Host:
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
Location:
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
Read more reviews

3. 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
Cleanliness:
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
Host:
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
Location:
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

4. Modern and minimalist studio near amenities

This comfortable studio is equipped with a fully equipped kitchen. There is a the grocery store at the ground floor of the building where you can get all that you need. The room has a balcony so whether you are checking-in for some staycation or sight-seeing, this place is perfect for you. Enjoy the breath-taking view of the skyline from its floor-to-ceiling windows. Getting to this location is easy. It’s just a train commute from the airport and walking distance to everything. This apartment studio is the place to choose if you want a hassle-free vacation. It’s also family-friendly, spotless, and safe. You can also access the pool deck and basketball court for some outdoor activities.

Steps to Mag Mile Shops & Pool/Gym with City View by Zencity
Chicago, Illinois, United States
186 reviews
Entire apartment 1 Bed 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
super surprised with the apt amenities
nice apartment and amenities would stay there again
the apartment was absolutely gorgeous with amazing views of the city
the space is comfortable and the amenities (ie the pool) are a huge bonus
liked the amenities in the apartment complex such as the pool area and gym
Cleanliness:
very clean and cozy
condo was clean and large for studio
apartment was very clean
the place is great very clean and stylish
place is very clean and enjoyable
Host:
the hosts are great quickly respond to any questions
quick and responsive replies
the host was very helpful and communicated very quickly
host was helpful about luggage storage and check in/out was so smooth
the check in process is easy and the door staff were very generous
Location:
cute and comfortable apartment with great location
the location is perfect
great location and nice place
awesome location really close to subway stations and restaurants and the magnificent miles
it is a great location that is close to everything
Read more reviews

5. 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
Cleanliness:
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
Host:
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
Location:
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

6. 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 location Downtown apartment Nice view 2
Chicago, Illinois, United States
170 reviews
Entire apartment 2 Beds 1 Bedroom 1 Bathroom
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
Cleanliness:
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:
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
Location:
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
Read more reviews

7. 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

8. 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
Cleanliness:
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
Host:
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
Location:
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

9. Simple studio in a great location

This small but comfortable studio that offers long-term stay is strategically located near everything that you need to go to — Lincoln Park, bars, coffee shops, restaurants, and even the beach. It has a simple kitchen and bathroom. It has a comfortable queen-size bed that’s perfect for a good night’s rest after a day of strolling and sight-seeing. This space is located in a safe neighborhood near Division Street in downtown Chicago. Self check-in is available for this accommodation.

The Basecamp - Downtown, Chicago (Long Term)
Chicago, Illinois, United States
87 reviews
Entire apartment 1 Bed 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
the room isn't extra special but the area is fantastic
would have been nice with a tv
pretty basic amenities but clean comfortable and easy to check in and out
i had a wonderful time in chicago and the apartment was perfect for my stay
it's a studio with a very comfortable bed working area and an equipped kitchen
Cleanliness:
perfect clean and big enough for 2
the apartment is very clean and the bed comfortable
despite being small and a bit dated everything was very clean
good clean little studio in a nice part of town
the apartment was clean and provides everything you need
Host:
krill was a great host
kyril was a great host and very responsive to our messages
host responded to messages very quickly and check in process was easy
kirill was really nice and helpful to help us with some logistics
kirill was a great host and was attentive to us every step of the way during our stay
Location:
great location in old town
location was great
nice location and good price
great location by the park close to dining beautiful streets to wander down
a good location which is very near to cta red line
Read more reviews

10. 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
Cleanliness:
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
Host:
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
Location:
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

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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