Vacation rentals with a patio in Woodlawn, Chicago

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Popular amenities for Woodlawn, Chicago patio rentals

Apartment rentals with a patio

Superhost
A living area features a dark sectional sofa paired with a cozy armchair, complemented by a decorative rug on tiled flooring. A wall-mounted TV is positioned above a sleek media stand. Light enters through an archway leading to the kitchen, which is partially visible.
Apartment in Chicago
4.86 out of 5 average rating, 114 reviews

Lovely 2-bedroom apartment in Pilsen

BarboraRating, 5 stars2 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 favorite
A bright living room features a cozy seating arrangement with a variety of armchairs and a sofa. Original art pieces adorn the walls, and a coffee table with a decorative table runner sits on a soft area rug. Light streams in through windows creating a lively atmosphere.
Apartment in Forest Park
4.99 out of 5 average rating, 156 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 favorite
A bright living room features hardwood flooring and a large, comfortable gray sectional sofa. Two unique yellow chairs are positioned nearby. A stylish TV unit and shelves display decor items, while light streams in through multiple windows, enhancing the open and inviting layout.
Apartment in Andersonville
4.99 out of 5 average rating, 155 reviews

Vibrant & Chic Apt On Quiet St in Andersonville

DianeRating, 5 stars2 weeks ago
Staying with Johana was a pleasure. The location was perfect, the house was cozy and clean. Highly recommend.
Guest favorite
A two-story apartment building is shown, featuring a light-colored exterior with dual-tone siding. Lush greenery surrounds the structure, including shrubs and grass. A staircase leads to the entrance, while the nearby homes display varying architectural styles.
Apartment in Forest Park
4.82 out of 5 average rating, 284 reviews

Home in Forest Park downstairs.

ChrisRating, 5 stars2 days ago
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
Superhost
A spacious living area features a large, L-shaped sectional sofa in a muted tone, accompanied by decorative pillows. A round mirror reflects the soft lighting, while vibrant artwork adorns the walls, contributing to a welcoming ambiance. A patterned area rug adds warmth underfoot.
Apartment in Merrillville
4.88 out of 5 average rating, 98 reviews

Lovely 1 bed room apartment, all to yourself.

ElizabethRating, 5 stars2 weeks ago
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.
Top guest favorite
A comfortable living area features a tufted dark sofa adorned with decorative pillows. A patterned accent chair complements the space. Wall art adds visual interest above a low coffee table set on a vibrant area rug, enhancing the inviting ambiance of the room.
Apartment 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 favorite
The living room features a spacious teal sofa paired with a simple black coffee table in front. A window with sheer curtains allows natural light to fill the area, complemented by a floor lamp and potted plants. Hardwood floors add warmth to the room.
Apartment in Berwyn
4.9 out of 5 average rating, 304 reviews

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

Ann-MaryRating, 5 stars3 days ago
Christine and Dan are responsive, communicate quickly and are very friendly!
Guest favorite
A charming garden unit is situated within a light-colored, two-story building, framed by a white picket fence. The entrance is marked by a set of steps leading to a spacious porch, where seating may be present. Nearby trees and greenery accentuate the inviting exterior.
Apartment in Irving Park
4.91 out of 5 average rating, 53 reviews

Montrose Gardens

JoyceRating, 5 stars6 days 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

Guest favorite
A modern two-story townhome is framed by lush greenery and an inviting lawn. Large glass windows allow natural light to brighten the façade. A paved walkway leads to the front door, flanked by neatly arranged steps and planters, contributing to the welcoming entrance.
Home in Hyde Park
4.94 out of 5 average rating, 34 reviews

Modern Family Townhouse

MarceaRating, 5 stars1 week ago
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!
Guest favorite
A modern living area is showcased with a cozy sectional couch in a warm orange hue. A flat-screen TV is mounted above a sleek fireplace, framed by dark paneling. Two round mirrors and side tables with lamps are positioned on either side, enhancing the space's contemporary design.
Home in Chicago
5 out of 5 average rating, 10 reviews

The Modern Muse of Chicago! Close to everything!

VictoriaRating, 5 stars6 days ago
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!
Superhost
A modern living area features a blue sofa and two cream-colored chairs arranged around a coffee table. A wall-mounted television displays a scenic view. The open layout seamlessly connects to a gourmet kitchen, which includes deep blue cabinetry and stainless steel appliances.
Home in Chicago
4.71 out of 5 average rating, 21 reviews

Lux_Home Chicago 8 mins Downtown

StephenRating, 5 starstoday
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 favorite
A living room features a cozy seating arrangement including a spacious sofa and armchairs, accompanied by a round coffee table. A fireplace is set beneath a wall-mounted television. Natural light enters through floor-length curtains, while decorative artwork adorns the walls.
Home in Chicago
4.93 out of 5 average rating, 30 reviews

Bronzeville Home! Downtown + McCormick + U of C

CynthiaRating, 5 stars1 week ago
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!
Guest favorite
A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.
Home in Wicker Park
4.97 out of 5 average rating, 246 reviews

Division St Designer Home In Heart of Wicker Park

MatthewRating, 5 stars2 weeks ago
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!
Superhost
A bright living space features an orange sectional sofa adorned with decorative cushions. Colorful wall art creates visual interest, while a small kitchenette with a bar height table and stools is visible. Natural light filters in through large windows, complementing the warm wood floors.
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 favorite
The living area features a cozy sofa and a patterned armchair, complemented by a glass coffee table. A television is positioned in one corner. Large windows invite natural light, while floor-to-ceiling curtains offer privacy. A potted plant adds a touch of greenery.
Home in Wilmette
4.97 out of 5 average rating, 154 reviews

Unique porcelain-enamel paneled "Lustron" home

JulietRating, 5 starstoday
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 favorite
The exterior of a ranch-style house features a well-maintained brick façade and a decorative iron front door. Lush green grass surrounds the walkway leading to the entrance, with small shrubs neatly placed along the edges. Large windows allow ample natural light into the home.
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.

Condo rentals with a patio

Guest favorite
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo 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 favorite
A spacious modern family room features a large sectional sofa adorned with decorative pillows. A 76” smart TV is mounted on the wall, displaying a beach scene. Natural light enters through multiple windows, illuminating the open layout that flows into a dining area with sleek furniture.
Condo in Pilsen Historic District
4.94 out of 5 average rating, 126 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

MelissaRating, 5 stars1 week ago
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!
Superhost
A modern kitchen area features white cabinetry and a central island equipped with a sink and stools. Stainless steel appliances are visible alongside a decorative backsplash. Natural light fills the space through overhead lighting and a nearby entryway.
Condo in Chicago
4.87 out of 5 average rating, 120 reviews

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

MelissaRating, 5 stars3 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.
Superhost
A living area features a leather sofa and two upholstered chairs, arranged around a glass coffee table. A brick accent wall provides character, while a large television sits atop a wooden console. Artworks adorn the walls, accompanied by natural light from the windows.
Condo in Logan Square
4.78 out of 5 average rating, 258 reviews

Logan Square Beauty with 2 Bedrooms W/parking

JamesRating, 5 stars2 weeks ago
Matt is a great host. Open, responsive and informative…everything you want really when on vacation
Top guest favorite
An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.
Condo in West Town
4.97 out of 5 average rating, 146 reviews

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

MichaelRating, 5 stars5 days ago
Great place! Everything was clean, in a good location and they communicated well.
Guest favorite
The modern kitchen features sleek white cabinetry and stainless steel appliances, including a refrigerator and oven. A central island provides extra counter space with two black stools positioned nearby. The open layout allows a view of the adjoining living area through a doorway.
Condo 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.
Guest favorite
A modern living area features a large black leather couch accompanied by a sleek armchair. Artistic Chicago-themed decor adorns the walls, including a vibrant sign. Natural light fills the space through window coverings, with a stylish area rug enhancing the warm ambiance.
Condo 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 favorite
A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.
Condo 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 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

Destinations to explore

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  5. Chicago
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  7. Rentals with a patio