
Holiday rentals with outdoor seating in Bridgeport, Chicago
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Top-rated Holiday Houses with Outdoor Seating in Bridgeport, Chicago
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Holiday House Rentals with Outdoor Seating

Chicago River House -BBQ Oasis now open!
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Unique porcelain-enamel paneled "Lustron" home
I enjoyed my stay here which enabled me to be close enough to Northwestern’s campus as I worked on a writing project. Being minutes from downtown Wilmette was a plus—be sure to check out Saint Roger’s Abbey bakery for wonderful French pastries! The house was neat, tidy, and matched the description. I also appreciated the record collection!

Casa PLZN Location | Entire Home | Garage Parking
We enjoyed our stay. Clean, nice house, and in a location convenient to everything we wanted to do. Host was very responsive when we had questions. We loved being so close to the train. Great restaurants around, and also a convenience store and Family Dollar right around the corner for anything you need!

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…

Boho Chic Coach House 30Min to downtown W/ Parking
It was a nice break from the hustle and bustle of the big city. A few great restaurants just a couple blocks away. And just a block away from bus stops.

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!

Clean, Cozy 1st Floor Flat, Kitchen, Parking
Great get away especially anyone in the architectural field. Great location in the suburbs of Chicago and has a great connecting train station near by that takes you into the heart of Chicago. Overall great stay!

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!
Apartment rentals with outdoor seating

iKlektik House Chicago / Robin
Mindy & Tony’s place is well located - easily walkable to transit & the cute West Town neighborhood restaurants & shops. The room was very nice - I especially liked enjoying sunset tea on the wisteria-covered deck. Thanks for a cozy stay!

Lovely 2-bedroom apartment in Pilsen
Very quiet neighborhood, the house is an easy 7min walk to the pink line. Quick ride to Chicago downtown. There is a cute bakery within walkable distance as well as a few grocery stores within a mile. The place itself looked exactly like pictures, very clean.

Cozy Luxurious Beauty - 10 Min to Downtown Chicago
Freddie was a great host. He responded right away when I had a little confusion & smoothed everything. The inside was beautiful & created a comfortable space to return after being out and about.

Best Location in Hyde Park apartment
Spacious and clean place in the quiet, convenient and safe area! The host is very friendly and response quickly when you have any questions!

Great Location & Bright 2BR+2BA | Mapletree Suites
Everything was great! From location to things to do, this is one of the best in the Windy City! 10 out of 10 would recommend!! 👍

*A Happy (City) Glamping- walk to train FREE park
The space is exactly as described. Loved how close it was to public transportation. The space is great for a weekend away.

Designer Avondale Attic
Just wonderful. That was one of the most beautiful accommodations I've ever been to. The apartment is totally lovingly furnished. Everything was super clean and tidy. There are even toothbrushes, toothpaste and a sleeping mask, if you need them. The kitchen is also super equipped with everything you need. The short walk to the metro was also very convenient. We would definitely come back.

Spacious 2BR on Quiet St - Free Park/Late Checkout
There isn't much to say that other's haven't mentioned. It's in a pretty good location, the neighborhood has a lot to offer. It is a touch away from the downtown hub but if you are willing to walk/take a ride share or cab it's not bad at all. Public transportation is an option we just didn't utilize it this time. The space is very nice. The Garretts' responded right away when asked about the AC. We did not encounter any issues. We enjoyed our stay. It was nice to have a washer and dryer to use. We had plenty of towels, etc.. Thank you for letting us stay. We would think about staying again if we all came, the distance to destinations would be the only question mark in the future.
Condo rentals with outdoor seating

A Stones Throw from U Chicago South Campus!
It was a very cozy apartment with a nice set up. Easy access to university of Chicago and the lakefront trail. We really enjoyed our stay!

3 BR Summer GetAway, 15mins to Loop+Gated Parking
Close to the green line for easy transportation.

The Urban Oasis | Outdoor Lounge • Sleeps 10+
The unit was as described, clean, affordable, easy to get to and home base from, and the neighborhood felt safe. There’s a coffee shop right on the corner we walked to in the mornings. We had a big group for a bachelorette and there was plenty of spaces to sleep downstairs (3 bedrooms with beds and one shared space with four beds), get ready (2 full bathrooms including two baths for kiddos), and lounge all together (large couch, big kitchen table, island seating, and outdoor covered area). Big thing for me is ceiling fans the bedrooms so that was super satisfying. Highly recommend this unit and we’d go back!

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
Great place! Everything was clean, in a good location and they communicated well.

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
John's place is great, just as described. Very clean and location is perfect (across the street from Pequod's). Check in/out was easy and communication was good.

Modern Chicago Movie Themed Apt
We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

Spacious 4 Bedroom Condo
We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.

Updated Designer Duplex In Fulton Market W/parking
Supurb stay in Fulton Market! Seth was an outstanding host—responsive, welcoming, and accomidating. The apartment was spotless, well decorated, and thoughtfully stocked with everything we needed for a comfortable stay. The beds and linens were especially cozy, making it easy to relax and feel at home. The location is superb—just steps away from a variety of highly rated restaurants. The location is superb—just steps away from a variety of highly rated restaurants. We also felt completely safe throughout our stay. The neighborhood has a welcoming, upscale vibe, which added to our peace of mind. A quick heads-up: the unit is a second-floor walk-up accessed via a private entry. Inside, as you can see has the spiral staircase; a unique architectural feature, but if you’re traveling with heavy luggage, it’s something to keep in mind. Pack accordingly! 😉 Overall, we had a wonderful experience and would gladly stay here again and agai
Quick stats about holiday rentals with outdoor seating in Bridgeport, Chicago
Total rentals
30 properties
Nightly prices starting at
$50 NZD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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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