
Holiday rentals with outdoor seating in Bridgeport, Chicago
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Top-rated rentals with outdoor seating in Bridgeport, Chicago
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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!

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!

Peaceful Family Home near Downtown, MDW, Free Park
This home was exactly as described. Was in a nice and pretty quiet neighborhood. Would stay here again.
Apartment rentals with outdoor seating

Lovely 2-bedroom apartment in Pilsen
Martha was very easy to work with and communicative! We didn’t explore around the location too much, but saw lots of options had we had the time. We had everything we needed and the unit was clean and cozy.

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!

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
We had a nice 2 night stay in Chicago. Place was affordable, comfortable and clean. 10 minutes from downtown Chicago and short walk to train. Hosts were friendly and great at communication.

Designer Avondale Attic
Einfach nur wundervoll. Das war eine der schönsten Unterkünfte, in der ich je war. Die Wohnung ist total liebevoll eingerichtet. Alles war super sauber und ordentlich. Es gibt sogar Zahnbürsten, Zahnpasta und eine Schlafmaske, falls man sie benötigt. Die Küche ist auch super ausgestattet mit allem was man braucht. Der kurze Weg zur Metro war ebenfalls sehr praktisch. Wir würden definitiv wieder kommen.

Spacious 2BR on Quiet St - Free Park/Late Checkout
This is the best Airbnb we've ever stayed in and we've been using Airbnb since the old days. The hosts have thought of everything you might need and the place is tastefully furnished and decorated. It's a place you would like to live rather than a neglected holiday home. It's in a lovely tree lined street within walking distance to the pink and blue line trains. There was parking available in the street. The kids enjoyed Stax - the pancake cafe just a block away. We were also able to walk to a chemist (CVS) and a supermarket (Jewel-Osco). There's a big kitchen which is fully stocked. There's lots of products in the bathroom if you forget something from home. The AC was effective (and we visited during a heatwave). The hosts let us check in early and communication was promot. We would recommend this place to friends and family.

Cozy 2BD APT near UC, Medical District, Downtown
Carinissimo appartamento per visitare Chicago ! Ho molto apprezzato la rapidità di risposta dei proprietari ma anche le informazioni ed i servizi che forniscono nella casa . Se torno a Chicago verrò nuovamente da voi , grazie mille
Apartment rentals with outdoor seating

A Stones Throw from U Chicago South Campus!
Luke was a responsive, helpful, and friendly host. Stones Throw is a great location for access to the University of Chicago, and it’s a short walk to the Metra for trips downtown. We really enjoyed our stay here, and the highlight was Luke’s invitation to participate in the rooftop honey harvest!

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!

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
The condo was a couple’s dream. Made you want to just live there forever. Very clean and felt like home. Hosts were communicative and courteous. Will definitely book again in the future and would highly recommend!

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
The condo was very spacious and had everything we needed to stay right at home. Adrian was responsive to our questions. It was a perfect distance from the city for exploring through the day but staying in a peaceful place at night. The staircase in the house was a little steep but otherwise it was perfect.

Wicker Park/Bucktown condo with large balcony
We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!

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
₹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
- Humboldt Park
- Six Flags Great America
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Brookfield Zoo
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Moraine Hills State Park