House holiday rentals in Downtown Chicago

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Popular amenities for house rentals in Downtown Chicago

House rentals with a pool

Home in Evanston
4.89 out of 5 average rating, 44 reviews

Beautiful Historic Colonial

AlexisRating, 5 stars5 months ago
Great weekend for our 25th reunion. We were 8 adults. Enjoyed the spacious dining room. Kitchen was well stocked. We hope to spend our next reunion weekend back at the house!
Home in Glen Ellyn
4.75 out of 5 average rating, 4 reviews

Pardizes Suites

AttiqRating, 5 stars2 weeks ago
We are so happy with experience. Host was supportive and place was spacious.
Guest favourite
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars4 months ago
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.
Top guest favourite
Home in Bloomingdale
4.94 out of 5 average rating, 47 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars5 days ago
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again
Top guest favourite
Home in Bensenville
5 out of 5 average rating, 33 reviews

New! Arcade+Sauna+Slots+Karaoke+more by O’Hare

BardoRating, 5 stars2 weeks ago
Couldn't believe such a beautiful place was so close to home. My kids loved it! The house was immaculate. They spent hours in the pool and I spent hours on the 95 inch TV watching the NCAA tournament highly recommended!
Guest favourite
Home in Schaumburg
4.96 out of 5 average rating, 27 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

LindsayRating, 5 stars3 months ago
Everything went perfect for us. We flew in from out of town, and some plans fell through. We asked Mike if it was possible to check in a couple hours early and he was very flexible. We really appreciate you and your home. Thanks for letting us stay.
Home in Chicago
New place to stay

Stunning Home in Prime Chicago

Weekly house rentals

Guest favourite
Home in Chicago
4.92 out of 5 average rating, 280 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

BrigidRating, 5 stars1 week ago
We enjoyed preparing pizzas from scratch in the perfectly sized kitchen with our adult kids who live in Chicago and their friends. There was plenty of space to sit around the spacious kitchen island and talk while cooking. The whole experience was made even better by using the Wolf stove top and Bosch wall-mount oven, which produced perfectly crisp crust and tasty toppings. The neighborhood felt safe and peaceful while providing everything we needed within walking distance. Parking was also easy. We had no trouble finding a space in front of the house all 4 days we were there. As a special bonus, a new chocolate cafe opened a few days ago (Hotel Chocolat Velvetiser Cafe) and is just a short walk away! We had a great time in this lovely home.
Guest favourite
Home in Glen Ellyn
4.92 out of 5 average rating, 144 reviews

Home in Glen Ellyn

RandyRating, 5 stars1 week ago
We loved our stay. The house was beautiful, the host was so easy to communicate and helpful with everything we needed.
Guest favourite
Home in Chicago
4.98 out of 5 average rating, 151 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Kevin And CourtneyRating, 5 stars1 month ago
Great experience at Casey’s place. The home is as well stocked with kitchen essentials and extras as any place that we have ever stayed. There were toys for the kids and the design of the place was awesome. We had a great stay and would definitely come back.
Superhost
Home in Blue Island
4.81 out of 5 average rating, 192 reviews

Warm and comfortable inviting Suburban home !

KevinRating, 5 stars2 weeks ago
Rich was a great host! Place was very comfy. I’d love to book again!
Guest favourite
Home in Chicago
4.86 out of 5 average rating, 221 reviews

The Avondale Guesthouse

ErickaRating, 5 stars6 months ago
We absolutely loved the place! Great location, price and space! Jed was so kind and responsive, and we absolutely loved the the outdoor space! We would definitely stay again!
Guest favourite
Home in Whiting
4.84 out of 5 average rating, 150 reviews

The Spa of Downtown Whiting

LeeRating, 5 stars3 weeks ago
Steven was a great host and his Spa in Whiting is a hidden gem. This is the second year we have stayed at Steven’s place and we’ll be going back!
Top guest favourite
Home in Chicago
4.95 out of 5 average rating, 183 reviews

Wrigleyville Greystone

ThomasRating, 5 stars3 weeks ago
Fantastic place in an awesome location. Very walkable part of town and a great spot to easily get to Wrigley Field. Found a number of great bars and restaurants in walking distance during our stay. Would definitely stay here again!
Superhost
Home in Wood Dale
4.76 out of 5 average rating, 160 reviews

Excellent Location for Vacation or Business Stays.

JamesRating, 5 stars3 months ago
This was our second stay at Rita’s and we found it very accommodating and great of an experience as our last visit. The neighborhood is in a great location and it is cozy and quiet. The property was extremely clean. We would be happy with staying here again in the future.

Private house rentals

Top guest favourite
Home in Oak Park
5 out of 5 average rating, 5 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars3 months ago
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.
Superhost
Home in Chicago
4.86 out of 5 average rating, 99 reviews

Casa PLZN Location | Entire Home | Garage Parking

CecilioRating, 5 stars2 weeks ago
Great place near restaurants and cafes. Garage access is a plus. Train noise is noticeable at first but you get used to it and it's only noise as the house doesn't rumble when the train passes.
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 38 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars5 months ago
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.
Top guest favourite
Home in Elmhurst
5 out of 5 average rating, 44 reviews

Big Family Home with 4 King Beds

LynnRating, 5 stars3 weeks ago
Great having pool table, wall mounted TV, and games in lower level. Appreciated comfortable beds, ample supply of glasses, bowls, flatware, and plates &, large dining space. Clean home, safe & quiet neighborhood, with easy access to major roads & O'Hare. Host provided clear & simple check in instructions
Superhost
Home in Chicago
4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

SaifRating, 5 stars6 months ago
The accommodation was spacious and very comfortable for our large group of 16. While the floors creak a bit, it wasn’t an issue. Samantha was always quick to address any questions and issues. The gated parking area provided ample space for our cars, which was a great convenience.
Superhost
Home in Wood Dale
5 out of 5 average rating, 4 reviews

Home in the Woods!

MaikoRating, 5 stars5 days ago
We had such a wonderful time at Jazmin Airbnb. The place was clean and smell great! She was very responsive and we had no issue with checking into our Airbnb. Thank you for being such a great host!
Top guest favourite
Home in Chicago Ridge
4.93 out of 5 average rating, 123 reviews

Quiet cul-de-sac with huge fenced in backyard

MichaelRating, 5 stars2 weeks ago
Absolutely loved staying here. Tom was an awesome host. He has very detailed instructions throughout the house for everything from connecting to the WiFi to how the individual tvs work. The couch in the living room is stupid comfortable and the master bedroom was cool and dark. 10/10 would stay here again
Superhost
Home in Chicago
4.84 out of 5 average rating, 500 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

ChrisRating, 5 stars1 week ago
Felt safe in the area . Easy parking . Close to CTA train and one stop away from our destination. Clean and quiet home felt like home also . I highly recommend this place if you attending any event at the united center and want to visit cloud gate easy directions. Joyce thanks for the wonderful stay .

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