
Holiday rentals with outdoor seating in Bridgeport, Chicago
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Top-rated rentals with outdoor seating in Bridgeport, Chicago
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
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Popular amenities for outdoor seating rentals in Bridgeport, Chicago
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.

Clean, Comfy 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!

Chicago's Bridgeport Huge 4 Story w/Garage Parking
We had a great time in Laura's place, wonderful neighborhood

Modern SFH Near McCormick Place & Soldier Field
Stayed with 4 adults and 5 kids. House was more than spacious and cozy. Furniture was nicely kempt. Beds were comfortable. Neighborhood was quiet. We rented a car and appreciated the garage to keep car in. We did have an issue with water temperature but was resolved quickly with host We loved the house!
Apartment rentals with outdoor seating

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 PacMan
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!

*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.

Breathtaking & Chic Oasis Loc in Desirable Old Twn
The apartment was great - the building was lovely, especially the gym which was great to be able to use. Super close to multiple bus stops and an L line, which made getting around super easy. The apartment itself was clean and looked like the pictures! Only downside was I that I was not able to check in on time, however I was able to drop bags off, which was really helpful, and they were super responsive to any question or concern I had during my stay. Would definitely stay here again!

Spacious Bronzeville Apartment
Really enjoyed our stay. Great transport links in and out of the city, being close to two train stations, but out the way enough to enjoy a quieter and more local perspective on Chicago. Easy to access, clear instructions and the host was fantastic. Well presented and clean within, as well as being far bigger than expected! Nice little touches inside too, such as plenty of coffee, a bottle of red wine and pasta bolognaise if we chose to stay in. Overall, really enjoyed our stay and would absolutely recommend.

Cozy 2BD APT near UC, Medical District, Downtown
Nice little quiet place. Owner was responsive when contacted, would definitely stay here again!
Apartment 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
Great accommodations for our family of 5. It's nice to have 3 bedrooms with all queen beds so everyone has ample room. Very clean. Responsive, attentive host. Would stay here again! Thanks!

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Wendy and Matt's place was comfortable and homey. The location was great, the apartment comfortable, and we had essential amenities. The building is mid-century modern and designed by famed architect Harry Weese that incorporates thoughtful references to Chicago architectural history throughout while still remaining visually cohesive. One minor issue is the stove, which is electric and somewhat underpowered. It's good enough for minor work like breakfast or heating leftovers but you may struggle producing more elaborate meals. It was a very minor quibble but worth noting for those culinarians wanting to prepare their own meals. The oven is decent but there is only one. Overall, my stay was excellent and I recommend Wendy and Matt's place wholeheartedly. They are excellent hosts as well.

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.
Quick stats about holiday rentals with outdoor seating in Bridgeport, Chicago
Total rentals
30 properties
Nightly prices starting at
₹2,579 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