Apartment holiday rentals in Chicago

Find and book unique apartments on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Chicago apartment rentals

Weekly apartment rentals

Top guest favourite
Flat in West Ridge
5 out of 5 average rating, 29 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

ElizabethRating, 5 stars3 days ago
This is a charming and very comfortable unit. All the amenities are thoughtful and more generous than most other AirBNBs that I’ve stayed. We found the location very convenient to family and Northwestern U, and even getting downtown. The unit was spotless, clean and organized. And exceeded our expectations. Being able to park in the garage was a huge benefit for us. We had a busy schedule with leaving in the morning and not getting back until later evening. It was so nice not to have to search for street parking and not have that worry. We very much enjoyed our stay. This will be our “place” when we return. Elizabeth
Superhost
Flat in Chicago
4.73 out of 5 average rating, 11 reviews

Cool spot in cool neighborhood

JulietteRating, 5 stars1 month ago
Next to the trains, a apartment with separate bedroom, living room, kitchen and bathroom, even a laundry room available if necessary and a host who responds quickly and does not hesitate to give advice on Chicago. I highly recommend!
Guest favourite
Flat in Chicago
4.95 out of 5 average rating, 74 reviews

Travel To Chicago New City

JasonRating, 5 stars2 weeks ago
Khong was responsive, helpful, friendly and overall just a cool host! Khong gave us a sweet surprise when we got in and gave us local recommendations, we loved the Back of The Yards Coffeehouse and it was within walking distance. During the day it felt like a safe neighborhood, during the night it was very lively and full of people in the best way. Khong’s place was so clean and inviting. The backyard was peaceful with a beautiful view of the church. We did have a slight mishap occur when we lost the keys to Khongs place but he was very understanding and kind about the situation. Our stay was everything we hoped for and more. We would definitely return the next time we are in Chicago! 10/10 recommendation from my family and I
Guest favourite
Flat in Pilsen Historic District
4.94 out of 5 average rating, 51 reviews

Pilsen Modern Chic Retreat

ElinorRating, 5 stars4 days ago
Great stay, carmen was very responsive and the place is very modern and clean.
Top guest favourite
Flat in Forest Park
4.96 out of 5 average rating, 28 reviews

Scrumptious 2nd floor Abode

RachaelRating, 5 stars2 weeks ago
This was a wonderful stay and great home base to discover Chicago. Jordan and Jeremy were responsive and accommodating and have created a very cozy spot. I really appreciate the attention to detail and cleanliness. Lots of amenities in both kitchen and bathroom that were very helpful. I even got some decorating tips, what a cute place! Highly recommended!
Superhost
Flat in Berwyn
4.81 out of 5 average rating, 53 reviews

Private Garden APT/ Cozy/Warm

CalebRating, 5 stars4 days ago
Quiet and friendly neighborhood. Very walkable. Place had everything I needed for the stay. Will definitely return if I’m ever in the area again.
Top guest favourite
Flat in Irving Park
4.98 out of 5 average rating, 64 reviews

Pine Beam Sloth Apartment next to Blue Line

KristinaRating, 5 stars3 days ago
The apartment was impeccably clean. Was traveling for business had everything needed. It is loft style with open bedroom ceiling. Restaurants nearby
Guest favourite
Flat in Avondale
4.94 out of 5 average rating, 98 reviews

Modern 1-Bedroom w/ off-street parking space

CooperRating, 5 stars4 weeks ago
Great place to stay for the value. Everything you could need from a rental while being in an excellent location that was close to the trains and Logan Square. Would book again.

Private apartment rentals

Guest favourite
Flat in Chicago
4.91 out of 5 average rating, 123 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

JonathanRating, 5 stars1 week ago
Great place in a good location! Wonderful neighborhood. Was easy to find and near main road on a frontage road, but you would never know it by how quiet things are. Highly recommended.
Top guest favourite
Flat in Forest Park
4.99 out of 5 average rating, 156 reviews

Sunny 1 bedroom apartment 1 block from restaurants

EleanorRating, 5 stars2 weeks ago
Jim was a fantastic host. Very responsive and timely in his communications and support for our needs during our stay in their place. Their home was comfortable and well appointed with additional amenities you don't often see in AirBnB spaces, like N'espresso appliances and supplies. We would definitely consider repeat visits! Thank you, Jim!
Top guest favourite
Flat in West Town
4.92 out of 5 average rating, 360 reviews

Spacious & private! Free parking! Great location!

KendalRating, 5 stars1 week ago
This place was amazing to stay at! Perfect for couples or a solo trip. It was easy to access the location. Parking was pretty good with the only down side being having to maybe circle around the block a time or two to find a spot. But nothing crazy! The space was clean and cozy. The host was also amazing at communicating, always responding promptly. I would definitely visit here again!
Guest favourite
Flat in Berwyn
4.91 out of 5 average rating, 385 reviews

Private apartment with retro vibe

JessicaRating, 5 stars3 days ago
very kind and responsive host. very clear instructions. apartment is large, sunny, spacious and has the coolest retro vibe with super cool decorations. Good AC and very close to public transportation in case you want to explore the rest of the city or get downtown. Very quiet and safe neighborhood, and she even provided a parking pass for you at no cost. thank you Antoinette!
Top guest favourite
Flat in Oak Park
4.97 out of 5 average rating, 109 reviews

Cheerful Oak Park Apartment

StacyRating, 5 stars2 weeks ago
Spacious apartment with fun extras (puzzle, yoga mat, etc.)! It was easy-to-find and well-stocked with supplies, including thoughtful items for our use. It was clean and comfortable; we didn't use the kitchen at all as it was a very quick stay. The hosts are cognizant of the noise from the train and highway, and provide earplugs, sound machines, blackout shades, a fan, etc., to help ensure guests can sleep well. The local recommendations were great. Downtown Oak Park is about a 10-minute drive; we appreciated the ability to walk 5 minutes to a nice café or restaurant.
Guest favourite
Flat in Oak Park
4.87 out of 5 average rating, 655 reviews

Rockin' 2Bed steps to shops/food/train

JacelynRating, 5 stars2 weeks ago
It was a great stay! Super easy to find and get into, the neighborhood was very nice and the decor was super cute! The host was very helpful, and always would respond quickly! Would definitely recommend!
Guest favourite
Flat in Logan Square
4.96 out of 5 average rating, 124 reviews

Garden Unit Getaway-Bucktown

MichaelRating, 5 stars3 days ago
Keith was the perfect host. Communication was great. We loved the apartment and the location was perfect. We will absolutely stay here again.
Superhost
Flat in Irving Park
4.92 out of 5 average rating, 693 reviews

Explore Chicago from an Urban Sanctuary with Free Parking

GuillermoRating, 5 stars2 days ago
First time in Chicago and it couldn’t have gone better. The location was perfect due to our “tourist” activities, everything was pretty much walkable, and if not, the uber was relatively cheap. The room itself caught my wife and I COMPLETELY off guard. It was spacious, cozy, BEAUTIFUL aesthetic, and very, very comfortable. All in all, our stay here made my first time in Chicago a trip to remember. If I ever decide to come back, I will definitely be staying here again.

Apartment rentals with a hot tub

Guest favourite
Flat in Logan Square
4.98 out of 5 average rating, 103 reviews

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

BriantRating, 5 stars2 weeks ago
We stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.
Superhost
Flat in West Rogers Park
4.85 out of 5 average rating, 78 reviews

Spacious Beautiful Condo

SophiaRating, 5 stars3 days ago
We came for our daughter’s graduation and stayed a few extra days to tour the city. This place was perfectly located for both occasions. It was much more spacious than we expected, and everything was very clean. We especially appreciated the fresh towels and beddings. Our only wish is that the beds were a bit larger, especially the double bed, which would be more comfortable for a couple if it were at least a queen size. That said, the beds were very comfortable. Overall, we had a wonderful stay - definitely one of our best Airbnb experiences!
Guest favourite
Flat in West Loop
4.96 out of 5 average rating, 27 reviews

Skyline Oasis: City & Lake Views

NatalieRating, 5 stars2 weeks ago
Perfect weeklong stay in Chicago! The apartment is well equipped and makes you feel right at home. The building is connected via sky bridge to Jewel making it easy to grab groceries. The location cannot be beat - easy access to West Loop, Wicker Park, River North. The hosts were fantastic and flexible with our check in times. Looking forward to coming back!
Superhost
Flat in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars1 week ago
David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.
Top guest favourite
Flat in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars1 month ago
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.
Superhost
Flat in West Loop
4.83 out of 5 average rating, 119 reviews

Penthouse Near Fulton: Skyline, Spacious

ValerieRating, 5 stars1 week ago
SPECTACULAR!! This space is how you should visit Chicago. Breath taking views from this 33rd floor luxury penthouse apartment lives up to the hype. Our family of six were extremely comfortable in this 3 bedroom/3 bath unit. And for a person that likes cooking, the kitchen is spacious. Don’t pass on seeing Chicago from the views in this beautiful apartment.
Superhost
Flat in The Loop
4.69 out of 5 average rating, 49 reviews

Sentral 1 Bedroom Apt in South Loop Chicago

RichardRating, 5 stars1 week ago
Sentral worked great for us going to a graduation for a long weekend. Unit is exactly as described, modern, and clean. Kitchen utensils are reasonable while shelves and refrig are empty save for some coffee so if going to cook/eat be sure to bring everything such as butter, spices, etc. - a Trader Joes is 3 blocks away. Price is not cheap but is very convenient and easy so on balance okay for us. Front desk is very helpful and cheerful.
Top guest favourite
Flat in Belmont Cragin
4.98 out of 5 average rating, 119 reviews

Belmont Pleasures - hot tub / arcade gaming room

AustinRating, 5 stars6 days ago
Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.

Quick stats about flat rentals in Chicago

  • Total rentals

    6.4K properties

  • Total number of reviews

    3.1L reviews

  • Family-friendly rentals

    3.1K properties are a good fit for families

  • Pet-friendly rentals

    2.2K properties allow pets

  • Rentals with a pool

    840 properties have a pool

  • Rentals with dedicated workspaces

    3.9K properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Flat rentals