House holiday rentals in Bridgeport, Chicago

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Popular amenities for Bridgeport, Chicago house rentals

House rentals with a pool

Home in Glen Ellyn
4.83 out of 5 average rating, 12 reviews

Pardizes Suites

CrystalRating, 5 stars1 week ago
I was speechless when I walked in her house it was beyond beautiful nothing was out of place at all when I say she had everything you can think of to accommodate us all she had all the toiletries you could think of the kitchen was stocked with all kind of seasonings dishes she even stocked breakfast sausages she put balloons out she really out done herself she went above and beyond it was plenty of games there the rooms were beautiful the beds were so comfortable I didn’t want to get up it was the best airbnb I ever stayed in we were all blown away by how beautiful and clean and neat it was Lisa is a very great hostess you all make sure to book with her she is great
Guest favourite
Home in Munster
5 out of 5 average rating, 11 reviews

Munster hide away

ChristopherRating, 5 stars5 months ago
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.
Home in Lockport
4.55 out of 5 average rating, 11 reviews

Hidden GEM OASIS in Chicagoland

BesjanaRating, 5 stars1 month ago
Everything was great! The place was just as imagined.
Superhost
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!
Guest favourite
Home in Bloomingdale
4.92 out of 5 average rating, 51 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.
Superhost
Home in Lincoln Park
4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars5 days 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
Home in Skokie
New place to stay

Luxury fenced in modern ranch

PatriciaRating, 5 stars4 days 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!
Home in Glenwood
4.82 out of 5 average rating, 60 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

RoseRating, 5 stars2 weeks ago
I love the place. Very spacious! Hot tub and pool were everything!!! I’d definitely reserve again! My only critique is the beds were not very comfortable in either room and the $75p/d to heat the pool, to me, is kinda steep for what we pay for the house.

Weekly house rentals

Guest favourite
Home in Chicago
5 out of 5 average rating, 10 reviews

The Modern Muse of Chicago! Close to everything!

VictoriaRating, 5 stars6 days 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 favourite
Home in Chicago
4.93 out of 5 average rating, 30 reviews

Bronzeville Home! Downtown + McCormick + U of C

CynthiaRating, 5 stars1 week ago
Great place for my family to stay! Rides to downtown, Navy Pier and Hyde Park were short and the kitchen and living room were very spacious. Henok was very kind and flexible!
Guest favourite
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!
Guest favourite
Home in Chicago
4.93 out of 5 average rating, 44 reviews

Floresitas Oasis, your home in Chicago

Kawina RochelleRating, 5 starstoday
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…
Guest favourite
Home in Chinatown
4.93 out of 5 average rating, 27 reviews

3 bd/ 2ba with Free Parking Spot by McCormick

AadhyaRating, 5 stars1 week ago
Had an amazing experience!! Host was very quick with responding on text if there were any issues too.
Superhost
Home in Chicago
5 out of 5 average rating, 4 reviews

Luxury-Near Downtown & United Center-Sleeps 14

AlexisRating, 5 stars1 week 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!
Superhost
Home in Chicago
4.9 out of 5 average rating, 29 reviews

Executive Contemporary Duplex

KaylaRating, 5 stars3 days ago
Perfect location! Not far from the best things to do in the city. The neighborhood is quiet and safe. I would highly recommend!
Guest favourite
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!

Private house rentals

Superhost
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
Guest favourite
Home in Hyde Park
5 out of 5 average rating, 19 reviews

Amazing historic campus mansion!

ArunaRating, 5 stars4 weeks 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
Home in Avondale
4.74 out of 5 average rating, 23 reviews

Garden/unit/1+1/cosy

GabriellaRating, 5 stars2 weeks ago
First time staying at an Air Bnb and it was amazing. Instructions were very clear and the place had everything we needed!
Superhost
Home in Chicago
4.95 out of 5 average rating, 19 reviews

Warm bungalow in New City

JosefRating, 5 stars1 week 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
Home in Roseland
4.9 out of 5 average rating, 72 reviews

Experience Chicago from Our 3-Story Retreat

SylviaRating, 5 stars1 week ago
The home is lovely we are seniors so the steps were a little bit tricky for us. I thought it was a bit closer to town but that was my mistake but the home is very relaxing and perfect for a large group or family I would highly recommend this home and our host was exceptional
Guest favourite
Home in Burbank
4.83 out of 5 average rating, 23 reviews

Cozy getaway in the city.

CynthiaRating, 5 stars1 week 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.
Top Guest favourite
Home in Oak Park
5 out of 5 average rating, 41 reviews

Oak Park - Wine House!

AltheaRating, 5 stars1 week ago
Excellent place to stay if you want to be in a “suburban-feel” of the city: you’re in a neighborhood that is steps away from a “main street” walkable area with shops. The two parking spots are very convenient and the main floor is so thoughtfully decorated and furnished. Everything is 5 stars, just want to make a few notes: be wary of the stairs as they can be a little slippery if you don’t have any grippy socks or slippers and there is only one full bathroom so you’ll have to share this with the other guests, also there are blinds but no blackout curtains so you’ll wake up with the sun. The neighbors are very nice, but if the kids are out and about you will hear them clearly. Would 100% book again!
Superhost
Home in Cicero
4.71 out of 5 average rating, 277 reviews

Close2city 3 bedroom with private parking (MDW)

RubinaRating, 5 stars2 weeks ago
Daniel was very responsive and accommodating. The private parking was great and the neighborhood was close enough to get into the city with ease.

Quick stats about house rentals in Bridgeport, Chicago

  • Total rentals

    70 properties

  • Nightly prices starting at

    $34 NZD 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

  • Wi-Fi availability

    70 properties include access to Wi-Fi

Destinations to explore

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