
House vacation rentals in Bridgeport, Chicago
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Top-rated house rentals in Bridgeport, Chicago
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Popular amenities for Bridgeport, Chicago house rentals
House rentals with a pool

Pardizes Suites
Really nice and spacious place. Everything was clean and comfy.

Glen Ellyn Home
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.

Munster hide away
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Hidden GEM OASIS in Chicagoland
Excellent host! Fantastic property!

Whole House With Hot Tub And Spacious Bedrooms
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

Schaumburg Woodfield Pool House 4bedroom 2.5bath
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.

Stunning Home in Prime Chicago
Weekly house rentals

Duplex Home RoscoeVillage/Wrigley Free St Parking
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.

Home in Glen Ellyn
We enjoyed our night here. It provided a calm place to rest and plenty of space. Host was wonderful to work with.

Spacious Five Bedroom Home in Trendy Chicago Neighborhood
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.

Cozy at the Walter
Lovely cozy home perfect for what we needed. Loved the yummy extras she left for us in the kitchen:) The beds were comfortable and there were plenty of extra comforters for the cold nights! The heater worked amazingly well and the home smelled so nice of mild sandalwood from a diffuser in the living room. We felt right at home, and the location for us worked out well! Thank you!!

The Avondale Guesthouse
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!

The Spa of Downtown Whiting
a really awesome place. I highly recommend this place.

Wrigleyville Greystone
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!

Excellent Location for Vacation or Business Stays.
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

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath
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.

Casa PLZN Location | Entire Home | Garage Parking
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.

Gorgeous and Luxurious 3 BR Home
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.

Big Family Home with 4 King Beds
We were a family of 14. My 3 adult Kids and their spouses, my 6 grandkids, ages 2 to 21 years old. The number of beds fit us comfortably. The game/activity room was a hit with the kids especially. The dining room and kitchen dinning areas fit us well. We did have some issues, that Syed responded to quickly. Syed is a very nice man and a great host, however the house is in need of some minor repairs, the garbage disposal didn’t work, cabinets in the kitchen need repair, we had ants on the counter in the kitchen that we had to spray to get rid of. The railing going upstairs was coming out of the wall. Syed responded quickly to rectify most of these things. The house and bathrooms are clean, but the tub and showers need to be recaulked, They are showing signs of mold. I spoke with Syed about these issues and he assured me they will be taking care of all these things. I believe that he will. Overall it was a great place for a large family. It met our needs for the 4 days we were there.

Grand Victorian Mansion in Austin Area
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.

Warm and comfortable inviting Suburban home !
Always a pleasure staying with at Rich’s place

The Country Life! Entire House.
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.

Quiet cul-de-sac with huge fenced in backyard
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
Quick stats about house rentals in Bridgeport, Chicago
Total rentals
70 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- Six Flags Great America
- Museum of Science and Industry
- Lincoln Park Zoo
- Chicago History Museum
- The Field Museum
- 875 North Michigan Avenue
- Wicker Park
- Willis Tower
- Lincoln Park
- Skokie Country Club
- Garfield Park Conservatory
- Chicago Cultural Center
- Promontory Point
- Odyssey Fun World
- Flossmoor Golf Club
- Moraine Hills State Park
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