
Apartment holiday rentals in Chicago
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Top-rated apartment rentals in Chicago
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Popular amenities for Chicago apartment rentals
Weekly apartment rentals

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

Cool spot in cool neighborhood
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!

Travel To Chicago New City
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

Pilsen Modern Chic Retreat
Great stay, carmen was very responsive and the place is very modern and clean.

Scrumptious 2nd floor Abode
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!

Private Garden APT/ Cozy/Warm
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.

Pine Beam Sloth Apartment next to Blue Line
The apartment was impeccably clean. Was traveling for business had everything needed. It is loft style with open bedroom ceiling. Restaurants nearby

Modern 1-Bedroom w/ off-street parking space
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

Hidden Gem:Artsy Speakeasy in Historic Bronzeville
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.

Sunny 1 bedroom apartment 1 block from restaurants
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!

Spacious & private! Free parking! Great location!
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!

Private apartment with retro vibe
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!

Cheerful Oak Park Apartment
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.

Rockin' 2Bed steps to shops/food/train
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!

Garden Unit Getaway-Bucktown
Keith was the perfect host. Communication was great. We loved the apartment and the location was perfect. We will absolutely stay here again.

Explore Chicago from an Urban Sanctuary with Free Parking
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

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

Spacious Beautiful Condo
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!

Skyline Oasis: City & Lake Views
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!

Large Studio Apartment with no cleaning fee
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.

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop
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.

Penthouse Near Fulton: Skyline, Spacious
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.

Sentral 1 Bedroom Apt in South Loop Chicago
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.

Belmont Pleasures - hot tub / arcade gaming room
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
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
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