
House vacation rentals in Bridgeport, Chicago
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Top-rated house rentals in Bridgeport, Chicago
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Bridgeport, Chicago house rentals
House rentals with a pool

Hidden GEM OASIS in Chicagoland
Nico was very helpful and anything we needed he came right away or answered promptly even at late hours! the pictures honestly dont do this place enough justice it was even more pleasing in person! pool was up-kept and clean.

Rosemont 4BD2BA house with Pool
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

Celebrate at Hacjenda house
I had such a great time at the Hacjenda House! I came here with my dog for a peaceful getaway and it was exactly that. Lena set up the fireplace inside for me and I was cozy all night. Plenty of firewood in their backyard. Super spacious and beautiful inside and out. Their tub upstairs is also so spacious for a bath. Lena was so kind by checking in on me throughout my stay. I didn’t want to leave. I definitely want to come back.

Luxury Loft with Private Pool and Movie Theater
Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

Luxury fenced in modern ranch
It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!

LUXE - Movie Theater + Spa House
Nicholas was great house was really nice will definitely be back

Schaumburg Woodfield Pool House 4bedroom 2.5bath
Great stay - really the only option in the area with a sizable inground pool, awesome option for summer trip for those with kids . Excellent location minutes away from woodfield and nearby shopping, easy access to major highways. House is spacious. Would consider again for our family’s annual summer visit to nearby relatives

Luxe heated indoor pool/hot tub
Weekly house rentals

The Modern Muse of Chicago! Close to everything!
Jasna was an amazing host! The house was absolutely spectacular—truly even better than the photos. Every room felt thoughtfully designed and full of warmth, making it feel just like home. We had all the amenities we needed, which made our stay super comfortable and stress-free. It was the perfect setting for a special girls’ trip with my mom and sister. The neighborhood was peaceful and beautiful, adding to the relaxing vibe. We’ll definitely be back! Thank you again for everything, Jasna!

CasaNova Modern City Living
Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!

Garden/unit/1+1/cosy
Wonderful home close to train station. Very convenient and cozy. Would recommend!

Floresitas Oasis, your home in Chicago
Lizbeth was an amazing host. She’s responsive and attentive. The place was exceptional clean and had an amazing smell. I was there to celebrate my birthday and was pleasantly surprised upon entry when I was greeted with a personalized birthday message, fresh flowers and a bottle of wine. Anytime I reached out to Lizbeth, she responded expeditiously. Again, very attentive. My husband and I will definitely stay at her beautiful Oasis again. We felt comfortable and completely safe. Everything we wanted to do was a quick drive from the location. If you’re considering staying at her home, you will not regret it. If I could give more than 5 stars, I would. Thanks Lizbeth for being an incredible host Until the next time…

Executive Contemporary Duplex
Perfect location! Not far from the best things to do in the city. The neighborhood is quiet and safe. I would highly recommend!

Luxury-Near Downtown & United Center-Sleeps 14
Dan is a gracious host! He takes great pride in his property and making sure guests are comfortable and satisfied with their stay. I recommend this property to anyone who truly wants a home away from home stay! My family and I will book again next year!

Historic Hyde Park Gray stone (upper)
Absolutely stellar stay! Kymi’s Airbnb in Chicago was everything we hoped for and more during our time at ASCO. The home was beautifully decorated, exceptionally comfortable, and stocked with everything we needed. My family felt incredibly safe and at ease the entire time. Kymi herself was a dream host—warm, responsive, and genuinely hospitable. She graciously allowed us to extend our stay and have a late checkout, all without hesitation or hassle. Her kindness and attentiveness made the experience even more special. I highly encourage anyone visiting Chicago to stay at her amazing home—you won’t regret it!

7 Bed Oasis with 5 Baths, Hot Tub, Sauna, Game Rm
Patty was extremely responsive prior to our visit to Chicago, during and post our stay. She also immediately addressed and resolved our cosmetic and minor concerns. Patty was beyond accommodating, kind, accessible, and understanding of our needs and expectations as we were traveling from three different states and with family members ranging for the age of 3 to 85. We booked this Airbnb for our family of 16 for Easter weekend and EVERYONE loved it. It was important that our elders were comfortable, safe and enjoyed themselves, they were sooo impressed and happy. The space is huge and perfect for entertainment. There are a ton of activities available and enough room for everyone/couples to have their own bed/room. With 1.5 kitchens including two stoves, it was convenient, as we cooked breakfast, lunch, and dinner each day in large quantities. The home was beautiful, comfy and we felt right at home! We highly recommend and can’t wait to book this Airbnb for our next trip to Chicago!
Private house rentals

Stylish Haven Near Loop in Sought After Pilsen
The house was exactly what it shows in pictures. Everything was clean and impeccable. The neighborhood was also really safe and quiet. I would definitely be back!

Family Friendly Duplex/9 min from MDW/Free Parking
Very nice space to bring friends over

Lux_Home Chicago 8 mins Downtown
Everything was exactly as pictured, and the space was clean and comfortable. The location is quiet, which made for a peaceful stay. Evan was an excellent host—accommodating, kind, and flexible. He responded promptly to any questions and made the experience seamless. Would definitely stay again!

Amazing historic campus mansion!
Caryl was extremely helpful with a check in process and she introduced us the property as well as surrounding local attractions. We felt the place was warm and very spacious for our group and we had a pleasant stay.

Warm bungalow in New City
Jd’s space was as described, very spacious and accommodating for larger parties. There were snacks, drinks, and towels/linens for use as well as washer and dryer. Jd was also very responsive and a great host. I’d say the biggest drawback was the very creaky floors, with only 3 people staying here, every movement on the main floor was heard. Maybe if we had a larger party, it may have filled up and not been too bad? General Chicago advice for anyone booking: - When considering, be aware that traffic can play a factor in getting from A to B. This is nothing against this specific place or host, just something to be aware of. - You are best off if you rent a car! Paid so much in Ubers and Lyfts in and out of the city. - The roads around this side of town are really bad. All that said, if you prepare correctly and have a large party, this was a very quaint and accommodating stay overall.

"Big" Tiny House yard 20 minutes from Chicago
Nam is a responsive and proactive host. While the house is advertised as tiny, it's not as small as I was expecting. It is basically the size of a one-bedroom apartment, and the bathroom is huge. Everything was new and clean. Metra is very close, the village is walkable, and you're just a few minutes by car from almost any type of restaurant or store you'd want. I would gladly stay again.

Spacious whole apt near shopping and city
Host was very nice and helpful with our questions, nice neighborhood some noise but nothing too extreme & house was clean.

Cozy getaway in the city.
Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.
Quick stats about house rentals in Bridgeport, Chicago
Total rentals
70 properties
Nightly prices starting at
R357 ZAR 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
- 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
- Moraine Hills State Park