
Vacation rentals with a patio in Woodlawn, Chicago
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Top-rated patio rentals in Woodlawn, Chicago
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Popular amenities for Woodlawn, Chicago patio rentals
Apartment rentals with a patio

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.

Sunny 1 bedroom apartment 1 block from restaurants
Jim was a fantastic host. Very responsive and timely in his communications and support for our needs during our stay in their place. Their home was comfortable and well appointed with additional amenities you don't often see in AirBnB spaces, like N'espresso appliances and supplies. We would definitely consider repeat visits! Thank you, Jim!

Vibrant & Chic Apt On Quiet St in Andersonville
Staying with Johana was a pleasure. The location was perfect, the house was cozy and clean. Highly recommend.

Home in Forest Park downstairs.
Sabin's home is amazing and always a perfect stay for me when I'm passing through. Clean, updated everything and HUGE TV, comfy beds and pillows. And he's a great host and responds quickly if anything comes up. This is my 2nd stay and I'll be returning again next time I'm passing through

Lovely 1 bed room apartment, all to yourself.
We had a wonderful 7 day stay in this beautiful apartment. It is beautiful, clean, and comfortable. We felt right at home. The living room wa spacious comfortable, with a large TV, and a cozy fireplace unit. The kitchen had everything necessary to cook meals, plus a nice assortment of coffee and tea, along with a Keurig. The bathroom was fresh and clean with plenty of towels. The bedroom had a large, comfortable bed with fresh linens, a large closet, and quiet dedicated workspace. Laundry facility was accessible right outside our door. The area and building were clean and quiet, with a lovely enclosed backyard with picnic table. Cornelius was a very responsive, helpful, friendly host, who answered all our questions, and made sure we had all the information we needed to make our stay fun and easy. Check in process was very simple, and there is ample parking I highly recommend Cornelius and this lovely unit. You will be very pleased with your stay.

Cheerful Oak Park Apartment
Spacious apartment with fun extras (puzzle, yoga mat, etc.)! It was easy-to-find and well-stocked with supplies, including thoughtful items for our use. It was clean and comfortable; we didn't use the kitchen at all as it was a very quick stay. The hosts are cognizant of the noise from the train and highway, and provide earplugs, sound machines, blackout shades, a fan, etc., to help ensure guests can sleep well. The local recommendations were great. Downtown Oak Park is about a 10-minute drive; we appreciated the ability to walk 5 minutes to a nice café or restaurant.

The Green Bungalow: Charming 1-BR apt. with patio
Christine and Dan are responsive, communicate quickly and are very friendly!

Montrose Gardens
This was a very cute one bedroom apartment. It was perfect for my husband, myself and my daughter. Extremely clean. So sweet they left treats and snacks! Host was very nice and accommodating. Would definitely stay again!
House rentals with a patio

Modern Family Townhouse
My family of 5 including my elderly parents had a lovely stay at Rachel and David’s house for our son’s graduation from UChicago. It is in a quiet location that is very close to the university. The hosts were very friendly and flexible. The place is spacious, light and airy and extremely clean. The beds (especially the two large bedrooms upstairs) had usually comfortable beds. All in all it a 10 out of 10!

The Modern Muse of Chicago! Close to everything!
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!

Lux_Home Chicago 8 mins Downtown
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!

Bronzeville Home! Downtown + McCormick + U of C
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!

Division St Designer Home In Heart of Wicker Park
I traveled to Chicago for work and had a nice three-day stay here. The Airbnb is in a great location, clean, and well-equipped with thoughtful amenities. I particularly enjoyed the small library!

Animal House near Sox stadium
If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.

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!

Charming 3 bed home with private backyard
I had an absolutely wonderful experience staying at this Airbnb! From the moment I arrived, everything exceeded my expectations. The place was spotless, beautifully decorated, and exactly as described in the listing—if not better. It felt like a perfect blend of comfort and style.
Condo rentals with a patio

Lovely top floor 2BR/2BA, steps from everything!
We had a great time here. The place is really cozy and located in a nice neighborhood with plenty of stuff in walking distance. Totally worth it.

The Urban Oasis | Outdoor Lounge • Sleeps 10+
Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT
Awesome location, near lots of local restaurants, public transit and a major grocery store. China Town is a short bus ride away. The neighborhood itself is awesome, helpful neighbors and very friendly local vendors. The apartment itself is clean, inviting and has everything you could possibly need. Cory and Alexis were very inviting host, quick to respond to my questions and were very informative. I will be keeping this location in mind for my future Chicago travels.

Logan Square Beauty with 2 Bedrooms W/parking
Matt is a great host. Open, responsive and informative…everything you want really when on vacation

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 vacation rentals with a patio in Woodlawn, Chicago
Total rentals
110 properties
Nightly prices starting at
G$6,279 GYD before taxes and fees
Total number of reviews
3.7K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
90 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
- Flossmoor Golf Club