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House vacation rentals in Bridgeport, Chicago

Find and book unique houses on Airbnb

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Popular amenities for Bridgeport, Chicago house rentals

House rentals with a pool

A single-story house is set against a backdrop of trees, featuring a stone facade and a sloped roof. A winding driveway leads to a two-car garage on the right. Lush green grass surrounds the home, contributing to a serene environment.
Home in Lockport
4.58 out of 5 average rating, 12 reviews

Hidden GEM OASIS in Chicagoland

PeytonRating, 5 stars1 day ago
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.
Superhost
A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars1 month ago
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!
Home in Lemont

Celebrate at Hacjenda house

DianeRating, 5 stars2 months ago
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.
Superhost
A cozy loft area features exposed brick walls and wooden beams. A compact sleeping space includes a spacious bed covered in neutral bedding. Two white chairs and a small side table are positioned for seating, with a window allowing natural light to enter.
Home in Lincoln Park
4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars1 week ago
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!
Superhost
The exterior of a mid-century modern ranch home is displayed, featuring a flat roof and a large, contemporary garage door. Lush greenery surrounds the entrance, complemented by a well-maintained lawn. The driveway provides ample space for parking, enhancing accessibility.
Home in Skokie
New place to stay

Luxury fenced in modern ranch

PatriciaRating, 5 stars1 week ago
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!
A spacious living area features a large projector screen displaying a vibrant image. Comfortable seating surrounds a modern electric fireplace, while a potted plant and decorative artwork add subtle touches to the space. Natural light is invited through nearby sliding glass doors.
Home in Logan Square
New place to stay

LUXE - Movie Theater + Spa House

CarlosRating, 5 stars2 weeks ago
Nicholas was great house was really nice will definitely be back
Guest favorite
An inviting backyard scene features a sparkling in-ground pool surrounded by lounge chairs and shaded by greenery. The house's exterior showcases large glass doors that open onto the patio area, providing a seamless connection between indoor and outdoor spaces.
Home in Schaumburg
4.87 out of 5 average rating, 30 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

ElbertRating, 5 stars5 days ago
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
Superhost
An indoor heated pool is surrounded by large windows and glass doors, allowing natural light to fill the space. The vaulted ceiling features skylights and ceiling fans. A blue bench lines one side of the pool, creating a relaxed environment with views of the outdoor area.
Home in Skokie
New place to stay

Luxe heated indoor pool/hot tub

Weekly house rentals

Guest favorite
A modern living area is showcased with a cozy sectional couch in a warm orange hue. A flat-screen TV is mounted above a sleek fireplace, framed by dark paneling. Two round mirrors and side tables with lamps are positioned on either side, enhancing the space's contemporary design.
Home in Chicago
5 out of 5 average rating, 10 reviews

The Modern Muse of Chicago! Close to everything!

VictoriaRating, 5 stars1 week ago
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!
Guest favorite
A light-filled entryway displays a striking staircase with dark wooden steps and a crisp white wall. Marble flooring complements the modern aesthetic, while a glass door leads to the outside. Decorative wall sconces provide warm lighting along the staircase.
Home in Chicago
4.88 out of 5 average rating, 51 reviews

CasaNova Modern City Living

HelenRating, 5 stars1 month ago
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!
Superhost
The exterior of the garden-level unit is shown, featuring a yellow two-story building with large windows. A tree is visible in front, and a black wrought-iron fence frames the entrance. A set of stairs leads to the front door, providing access to the property.
Home in Avondale
4.75 out of 5 average rating, 24 reviews

Garden/unit/1+1/cosy

RobertRating, 5 stars5 days ago
Wonderful home close to train station. Very convenient and cozy. Would recommend!
Guest favorite
A modern kitchen features dark wood cabinetry paired with light granite countertops. Stainless steel appliances, including a refrigerator and oven, are enhanced by a stylish backsplash. A dining area with a square table and tall chairs is complemented by bar seating at the island.
Home in Chicago
4.93 out of 5 average rating, 44 reviews

Floresitas Oasis, your home in Chicago

Kawina RochelleRating, 5 stars4 days ago
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…
Superhost
An open-concept kitchen and living area features a modern design, highlighted by sleek cabinetry and a spacious island with seating. Natural light fills the room, accentuating the contemporary fixtures and appliances. A comfortable couch is positioned in the inviting living space, creating a perfect gathering spot.
Home in Chicago
4.9 out of 5 average rating, 29 reviews

Executive Contemporary Duplex

KaylaRating, 5 stars1 week ago
Perfect location! Not far from the best things to do in the city. The neighborhood is quiet and safe. I would highly recommend!
Superhost
An open-concept living area showcases modern decor with plush seating arranged around a coffee table. A large smart TV is mounted on the wall, complemented by artwork above the fireplace. Light hardwood flooring and a staircase lead to the upper level, creating a bright and inviting space.
Home in Chicago
5 out of 5 average rating, 4 reviews

Luxury-Near Downtown & United Center-Sleeps 14

AlexisRating, 5 stars2 weeks ago
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!
Guest favorite
A charming two-story building features a distinctive roofline with decorative elements. The front entrance is approached by a set of stairs, flanked by a wrought iron gate and a landscaped front yard with gravel and greenery.
Home in Washington Park
4.95 out of 5 average rating, 57 reviews

Historic Hyde Park Gray stone (upper)

FadiRating, 5 stars2 weeks ago
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!
Guest favorite
A spacious living area features a large sectional sofa accented with colorful cushions. A stylish coffee table sits on a decorative area rug. Bright overhead lighting illuminates the room, enhancing the open layout that connects to dining and kitchen spaces.
Home in Bridgeport
4.93 out of 5 average rating, 72 reviews

7 Bed Oasis with 5 Baths, Hot Tub, Sauna, Game Rm

TiokoRating, 5 stars2 months ago
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

Superhost
A well-lit living area features a comfortable gray couch paired with a stylish armchair. A circular coffee table sits atop a light wood floor. A wall-mounted TV is prominently displayed, while a console table holds decorative items and baskets, providing a warm and functional space.
Home in Pilsen Historic District
4.75 out of 5 average rating, 117 reviews

Stylish Haven Near Loop in Sought After Pilsen

GianfrancoRating, 5 stars4 days ago
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!
Superhost
A spacious living area features a large sectional sofa adorned with colorful throw pillows. Sunlight streams through multiple windows, illuminating a light-colored rug. A ceiling fan is positioned above, and a modern television mounted on the wall complements the neutral tones.
Home in West Lawn
4.92 out of 5 average rating, 48 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

EhjayRating, 5 stars2 weeks ago
Very nice space to bring friends over
Superhost
A modern living area features a blue sofa and two cream-colored chairs arranged around a coffee table. A wall-mounted television displays a scenic view. The open layout seamlessly connects to a gourmet kitchen, which includes deep blue cabinetry and stainless steel appliances.
Home in Chicago
4.71 out of 5 average rating, 21 reviews

Lux_Home Chicago 8 mins Downtown

StephenRating, 5 stars4 days ago
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!
Guest favorite
The exterior of a historic brick home features a prominent gable roof and leaded windows. Lush greenery surrounds the property, highlighted by manicured shrubs and trees. A pathway leads to a welcoming entrance, inviting guests to explore the beautiful architecture of the residence.
Home in Hyde Park
5 out of 5 average rating, 19 reviews

Amazing historic campus mansion!

ArunaRating, 5 stars1 month ago
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.
Superhost
The exterior of a spacious brick house is displayed, featuring large windows that allow natural light to enter. A well-maintained garden with blooming flowers is visible in front, while a secure black fence surrounds the property, enhancing privacy.
Home in Chicago
4.95 out of 5 average rating, 20 reviews

Warm bungalow in New City

JosefRating, 5 stars2 weeks ago
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.
Superhost
A cozy living area features a gray sofa with decorative pillows positioned against a light-colored wall. A small coffee table sits on a textured area rug, and a wall-mounted television is visible above. Natural light enters through a nearby door, complemented by simple window treatments.
Home in Westmont
4.69 out of 5 average rating, 13 reviews

"Big" Tiny House yard 20 minutes from Chicago

RyanRating, 5 stars1 week ago
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.
Superhost
The living area features a teal sofa and a mustard yellow armchair arranged around a glass coffee table. A small plant decorates the table, while light enters through a window adorned with greenery. A wall display adds a touch of color to the space.
Home in Cicero
4.79 out of 5 average rating, 193 reviews

Spacious whole apt near shopping and city

CassieRating, 5 stars2 weeks ago
Host was very nice and helpful with our questions, nice neighborhood some noise but nothing too extreme & house was clean.
Guest favorite
A modern dining area features a large marble table set with plates and utensils, surrounded by upholstered chairs. Pendant lights illuminate the space, highlighting the sleek kitchen in the background, equipped with stainless steel appliances and white cabinetry.
Home in Burbank
4.83 out of 5 average rating, 23 reviews

Cozy getaway in the city.

CynthiaRating, 5 stars2 weeks ago
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

Destinations to explore

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