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Vacation rentals with a patio in South Side

Find and book unique patio rentals on Airbnb

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Popular amenities for South Side patio rentals

Apartment rentals with a patio

Superhost
A small outdoor patio features a round table with two chairs, set on a patterned stone surface. Natural light filters through the nearby windows, creating a relaxed atmosphere. Surrounding greenery adds a touch of nature to the space.
Apartment in Chicago
4.87 out of 5 average rating, 104 reviews

Lovely 2-bedroom apartment in Pilsen

AnaRating, 5 stars1 week ago
Buena locación y dentro de un vecindario tranquilo
Guest favorite
A private balcony features wooden flooring and is lined with brick walls. Two wicker chairs with blue cushions are positioned beside a small folded table. A railing extends along the front, providing a view of the surrounding area.
Apartment in Chicago
4.94 out of 5 average rating, 69 reviews

Spacious! 3 bedroom apartment in Edgewater!

PatrickRating, 5 stars1 month ago
Awesome apartment in the Loyola Chicago neighborhood. Easy access to the loop with the red line. Host is super responsive. The place was spotless and well stocked when we arrived.
Guest favorite
A cozy living area features two large windows allowing natural light to fill the space. A fold-out futon sofa and a black armchair are positioned around a wooden coffee table. An adjacent kitchenette with a two-seat dining table is visible, along with various plants enhancing the atmosphere.
Apartment in Chicago
4.92 out of 5 average rating, 102 reviews

Spacious 1BR Garden Apt & Parking

TomásRating, 5 stars6 days ago
Mikael's place was amazing. Unlike most places listed around Hydde Park in Chicago, Mikael's place had from great reviews and they were totally right. The place is very well kept, spacious, practical, with very calm surroundings. I had great sleep and having breakfast while looking at the garden was a big plus for me too. I had no issues regarding privacy or noise which is something commonly brought up in listings in this sector, especially in old buildings. Mikael was also very responsive and kind. If I ever go back to Chicago I would definitely consider staying here again.
Guest favorite
A modern living space features a dark sofa adorned with colorful cushions. A round coffee table sits in front, accompanied by a small side table with a decorative vase. A large mirror reflects the cozy atmosphere, while a vibrant city skyline artwork adds visual interest to the wall.
Apartment in Chicago
4.97 out of 5 average rating, 106 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

ÁlvaroRating, 5 stars1 month ago
El apartmento es cómodo, muy limpió y amplio para 4 personas. La zona nos pareció agradable y tranquila. Además está bien conectada, la estación de metro está cerquísima. Lo único que no nos gustó es no poder regular nosotros el termostato de la calefacción.
Top guest favorite
A cozy kitchen and dining space showcases wooden cabinetry and modern appliances. Two patterned chairs are positioned around a round table, while a brown sofa adorned with colorful cushions adds comfort. Sunlight filters through yellow drapes framing a window, enhancing the inviting environment.
Apartment in Chicago
4.97 out of 5 average rating, 39 reviews

2 Room Apartment in Vintage Bldg

AudréanneRating, 5 stars4 days ago
We loved the apartment. It is ideally situated and was perfect for our little dog. The area is really nice an peaceful. It was also easy to get downtown via the red line. Karen was a fantastic host. We appreciated all the little gestures and the fact that she had saved a parking spot for us upon our arrival. We would come back anytime.
Superhost
A light-colored sectional sofa occupies the living area, accompanied by a dark wooden coffee table. A large piece of artwork featuring mountainous scenery is displayed on the wall, while natural light enters through the sliding doors, creating a serene atmosphere.
Apartment in Glenview
4.86 out of 5 average rating, 28 reviews

1 Bedroom Apartment/free parking

DarrenRating, 5 stars1 month ago
We stayed at Karolinas apartment for 7 months and she was a wonderful host. She quickly addressed any problems. For example, we locked our keys in the apartment. I texted her and a new set of keys were promptly delivered. The apartment itself is super comfortable. Great furniture and appliances and we enjoyed the outdoor balcony. I would highly recommend renting from Karolina and this apartment specifically. We have no complaints and our stay was wonderful. Thank you Karolina!
Guest favorite
The exterior of a Victorian home is showcased, featuring a welcoming porch with steps leading to the entrance. A white picket fence surrounds a manicured garden, complemented by lush greenery and a decorative arch, creating an inviting approach to the residence.
Apartment in Chicago
4.95 out of 5 average rating, 21 reviews

Tree-Lined Street Near the Lake!

KarenRating, 5 stars1 month ago
This place has the best location. It was easy for me to take the Brown line and get around town. Cute coffee shop bakery on the corner. Mark and Carmen where friendly when we meet in the garden. Nice stay!
Top guest favorite
A spacious patio area is arranged with a large table surrounded by red chairs, under a vibrant red umbrella. A gas grill is positioned nearby on a paved surface, with lush greenery and colorful flower pots adding to the inviting outdoor setting.
Apartment in Chicago
5 out of 5 average rating, 24 reviews

Garden Apartment- RickStan Manor

AngeloRating, 5 stars6 days ago
Places is great. Easy access to train that can take you downtown, Lord of restaurants, supermarket and pharmacy around on a very peaceful neighborhood. Stanley was great host all around and house was awesome. Highly recommended

House rentals with a patio

Superhost
Home in Berwyn
4.9 out of 5 average rating, 31 reviews

European Custom Built Home

DanRating, 5 stars1 month ago
the home was fantastic. it fit our need perfectly! thank you for a fantastic stay.
Superhost
Home in Chicago
4.92 out of 5 average rating, 39 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars1 week ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Guest favorite
A modern kitchen is showcased with stainless steel appliances, including a microwave and gas stove. White cabinetry complements the granite countertops. A small breakfast bar with two stools is present, alongside a decorative arrangement of plants and kitchen essentials.
Home in Hazel Crest
4.86 out of 5 average rating, 22 reviews

Your Peaceful,Joyful,Cozy, Relaxing, Experience

DouglasRating, 5 stars4 months ago
This is definitely a gem in the middle of the South Suburbs. The place was really decorated nice, made us feel comfortable and right at home. Erica is a really great host and she is very attentive to any concerns we may have had during our stay. The neighborhood was really quiet and there was a park right on the corner for me to walk my puppy every morning. You will be pleased with this one. I recommend this place to anyone that wants to get away from the hustle and bustle of the big city and wants to enjoy quiet Suburban surroundings. I would definitely stay again, in fact I plan to.
Guest favorite
The exterior of a charming two-story home is displayed, featuring a pitched roof and bright blue front door. A colorful arrangement of orange and yellow tulips blooms in the foreground, contrasting against the greenery of the well-maintained lawn and the soft siding of the house.
Home in Chicago
4.97 out of 5 average rating, 29 reviews

Wrigley classic+trendy+2garage

JulieRating, 5 stars2 weeks ago
This is a great property. We had a fantastic stay in Chicago. It was so clean and just like the photos. Very spacious and ideal for families. Thank you.
Superhost
An enclosed outdoor space is framed by walls featuring greenery and light blue siding. A small white table is positioned on a concrete surface. Steps lead to an elevated area, enhancing accessibility and inviting relaxation.
Home in Chicago
4.86 out of 5 average rating, 100 reviews

Casa PLZN Location | Entire Home | Garage Parking

CecilioRating, 5 stars3 weeks ago
Great place near restaurants and cafes. Garage access is a plus. Train noise is noticeable at first but you get used to it and it's only noise as the house doesn't rumble when the train passes.
Guest favorite
A two-story home is presented, showcasing a warm-toned brick exterior. A spacious deck is attached, featuring a dining area and comfortable seating. String lights are hung overhead, adding a cozy touch. The surrounding area includes neighboring buildings and a well-maintained outdoor space.
Home in Chicago
4.95 out of 5 average rating, 38 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars6 months ago
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.
Superhost
A single-story brick home is framed by well-maintained greenery and a manicured lawn. Large windows are visible, allowing natural light into the interior. Neat hedges surround a circular garden bed filled with flowers, creating a welcoming entrance.
Home in Richton Park
4.86 out of 5 average rating, 14 reviews

Home away from home

KennyRating, 5 stars1 week ago
Delbert’s place was nice, and Delbert was a good host. Would definitely stay again.
Top guest favorite
A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.
Home in Chicago Ridge
4.93 out of 5 average rating, 123 reviews

Quiet cul-de-sac with huge fenced in backyard

MichaelRating, 5 stars3 weeks ago
Absolutely loved staying here. Tom was an awesome host. He has very detailed instructions throughout the house for everything from connecting to the WiFi to how the individual tvs work. The couch in the living room is stupid comfortable and the master bedroom was cool and dark. 10/10 would stay here again

Condo rentals with a patio

Guest favorite
An outdoor seating area features a circular table surrounded by four comfortable chairs. A charcoal grill is positioned nearby against the wall, and a door leads to the interior. A grassy border and white fence create a relaxing atmosphere.
Condo in Chicago
4.95 out of 5 average rating, 103 reviews

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

JadeeRating, 5 stars3 days ago
The only thing is the parking situation but overall I give the place and the Host 10 star
Superhost
A wooden patio area is framed by an overhead structure with angled supports. Two simple chairs are positioned in the corner, surrounded by wooden decking. The ground is partially covered with snow, indicating a cool season, with greenery visible in the background.
Condo in Chicago
4.84 out of 5 average rating, 184 reviews

Loft-Like Wicker Park Condo Steps from the Cta!

KathyRating, 5 stars1 month ago
Great place! Very well kept and clean. Tom is very responsive from the time you book. Just be mindful that as stated there is NO where to park if you drive. All in all such a great neighborhood.
Guest favorite
A modern living area features a light-colored sectional sofa adorned with blue accent pillows. A round black coffee table is positioned in the center, resting on a decorative rug. Two lamps and a piece of coastal-themed artwork complement the bright, airy atmosphere.
Condo in Chicago
4.89 out of 5 average rating, 111 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars1 week ago
Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend
Guest favorite
A bright living area is illustrated with large windows allowing natural light to fill the space. A comfortable beige sectional sofa provides seating, while a wooden coffee table sits on an area rug. A desk with modern design and a chair are present, enhancing the workspace.
Condo in Chicago
4.92 out of 5 average rating, 113 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

SearaRating, 5 stars1 week ago
Great place to stay! Quiet neighborhood and walkable distance from a few shops and food places. We enjoyed our stay very much!!
Guest favorite
A modern kitchen features sleek white cabinetry and a spacious island with four orange bar stools. A stainless steel refrigerator and cooking range are visible, while soft overhead lighting enhances the contemporary design. A TV is mounted on the wall, providing entertainment options.
Condo in Chicago
4.93 out of 5 average rating, 117 reviews

Urban Oasis | Great for Families w/ Kids

ParkerRating, 5 stars1 week ago
We had a very good stay for a friends wedding a few blocks away in Chicago. As it is very modern, cozy, and clean. Alex's response time is very quick to whatever may arise. We would highly recommend staying there. Thanks for the stay!
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 Chicago
4.91 out of 5 average rating, 101 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

KathleenRating, 5 stars2 days ago
It was exactly as it was pictured except the front door is adjacent to a beauty salon and a bit hidden at first. The place was immaculate - very clean and the kitchen in particular was excellently appointed. It is on the third floor in an older building so there are stairs. The building was quiet. With gated and lit parking provided nearby our vehicle was safe.
Top guest favorite
An expansive street view patio features a railing and several seating options, including black chairs and a glass-top table. The view encompasses vibrant neighborhood storefronts and greenery, offering a glimpse of city life.
Condo in Chicago
4.98 out of 5 average rating, 116 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

AndrewRating, 5 stars6 days ago
Under the category of actions speak louder than words, I have stayed at Allan's place about five times, and it remains my first choice when visiting Chicago.
Superhost
A spacious living area is showcased, featuring a light-colored sectional sofa and a round coffee table. A ceiling fan is installed above, and natural light fills the room through large windows. The adjoining staircase leads to an upper level, complementing the open layout.
Condo in Chicago
4.86 out of 5 average rating, 145 reviews

Tri-Taylor/Medical Dist. near West Loop

MelindaRating, 5 stars2 weeks ago
We had a great time in your space. We had everything we needed!

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