Holiday rentals with a patio in Woodlawn, Chicago

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Popular amenities for rentals with patio in Woodlawn, Chicago

Flat rentals with a patio

Superhost
Flat in Chicago
4.86 out of 5 average rating, 114 reviews

Lovely 2-bedroom apartment in Pilsen

BarboraRating, 5 stars3 weeks ago
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.
Top guest favourite
Flat in Forest Park
4.99 out of 5 average rating, 157 reviews

Sunny 1 bedroom apartment 1 block from restaurants

EleanorRating, 5 stars2 weeks ago
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!
Top guest favourite
Flat in Andersonville
4.99 out of 5 average rating, 160 reviews

Vibrant & Chic Apt On Quiet St in Andersonville

GeorgeRating, 5 stars4 days ago
Johana’s place was a 10 ! Place was exactly as stated. Parking was always available and we even parked right in front of the building twice! Full size refrigerator and all the kitchen essentials were there. Beds were extremely comfortable with room darkening curtains. Felt safe walking around. We will be keeping our eyes open for her place being available for future visits.
Superhost
Flat in Irving Park
4.78 out of 5 average rating, 143 reviews

⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

ErinRating, 5 stars2 weeks ago
It was in a great location, everything worked out perfectly and I would stay there again! It was really cute and comfortable.
Guest favourite
Flat in Forest Park
4.87 out of 5 average rating, 259 reviews

Home in Forest Park Upstairs.

AndrewRating, 5 stars3 days ago
We had a wonderful stay and he was a very responsive host! Will be staying again
Top guest favourite
Flat in Oak Park
4.97 out of 5 average rating, 109 reviews

Cheerful Oak Park Apartment

StacyRating, 5 stars2 weeks ago
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.
Guest favourite
Flat in Berwyn
4.9 out of 5 average rating, 304 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Ann-MaryRating, 5 stars6 days ago
Christine and Dan are responsive, communicate quickly and are very friendly!
Guest favourite
Flat in Irving Park
4.91 out of 5 average rating, 54 reviews

Montrose Gardens

JoyceRating, 5 stars1 week ago
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

Superhost
Home in Bronzeville
4.96 out of 5 average rating, 49 reviews

3bd/3ba Bronzeville Beauty

BrittanyRating, 5 stars2 months ago
The hosts’ of this property were great and accommodating. They catered to our altered schedule and compromised on a request of ours. We will definitely stay here again.
Superhost
Home in Chicago
4.71 out of 5 average rating, 21 reviews

Lux_Home Chicago 8 mins Downtown

StephenRating, 5 stars3 days ago
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!
Guest favourite
Home in Wicker Park
4.97 out of 5 average rating, 247 reviews

Division St Designer Home In Heart of Wicker Park

MindyRating, 5 stars4 days ago
This place was perfect for two of us! Everything about the description was accurate. It was very clean, super easy to access, and in a perfect spot-walkable to tons of restaurants, coffee shops, and even a few gyms we tried. Water pressure in the shower was phenomenal. Neighborhood felt safe for late night walking to and from restaurants. Hosts were communicative without being over-the-top. Would book again in a heartbeat!
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!
Superhost
Home in Bridgeport
4.72 out of 5 average rating, 54 reviews

Animal House near Sox stadium

ChristineRating, 5 stars1 month ago
If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.
Top guest favourite
Home in Wilmette
4.97 out of 5 average rating, 154 reviews

Unique porcelain-enamel paneled "Lustron" home

JulietRating, 5 stars3 days ago
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!
Guest favourite
Home in Chicago
5 out of 5 average rating, 6 reviews

Charming 3 bed home with private backyard

ToniaRating, 5 stars1 month ago
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.
Top guest favourite
Home in Kenwood
5 out of 5 average rating, 23 reviews

Villa Noir Chicago Victorian 7 min to downtown

EddieRating, 5 stars2 weeks ago
Great place. Great communication. Perfect for what we needed. Great house. Great neighborhood, right outside of downtown.

Apartment rentals with a patio

Guest favourite
Apartment in Avondale
4.96 out of 5 average rating, 117 reviews

Lovely top floor 2BR/2BA, steps from everything!

DanielRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Pilsen Historic District
4.94 out of 5 average rating, 127 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

BridgetteRating, 5 stars1 day ago
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!
Superhost
Apartment in Chicago
4.87 out of 5 average rating, 120 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

MelissaRating, 5 stars6 days ago
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.
Top guest favourite
Apartment in West Town
4.97 out of 5 average rating, 146 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

MichaelRating, 5 stars1 week ago
Great place! Everything was clean, in a good location and they communicated well.
Guest favourite
Apartment in Lincoln Park
4.91 out of 5 average rating, 110 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

NicolasRating, 5 stars1 week ago
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.
Superhost
Apartment in Near West Side
4.86 out of 5 average rating, 155 reviews

Tri-Taylor/Medical Dist. near West Loop

SusanRating, 5 stars2 weeks ago
The place was what we expected based on photos, and was accommodating for a family of 5 adults. The hosts were very responsive to a minor maintenance issue while being respectful of our privacy. The neighborhood was pleasant and accessible for the activities we were interested in.
Guest favourite
Apartment in Ukrainian Village
4.93 out of 5 average rating, 139 reviews

Modern Chicago Movie Themed Apt

LechelleRating, 5 stars2 weeks ago
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!
Guest favourite
Apartment in West Town
4.98 out of 5 average rating, 165 reviews

Spacious 4 Bedroom Condo

ScottRating, 5 stars1 month ago
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 a patio in Woodlawn, Chicago

  • Total rentals

    110 properties

  • Nightly prices starting at

    $39 SGD 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Woodlawn
  7. Rentals with a patio