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Holiday rentals with a patio in South Side

Find and book unique rentals with patio on Airbnb

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Popular amenities for rentals with patio in South Side

Flat rentals with a patio

Superhost
Flat in Chicago
4.88 out of 5 average rating, 112 reviews

Lovely 2-bedroom apartment in Pilsen

BarboraRating, 5 stars6 days 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.
Guest favourite
Flat in Chicago
4.92 out of 5 average rating, 142 reviews

Modern 3BR with Private Rooftop & Free Parking

JillRating, 5 stars1 week ago
Song’s place was perfect for our family trip to Chicago!
Top guest favourite
Flat in Chicago
5 out of 5 average rating, 22 reviews

Al Capone Era Speakeasy 3 BRs

TimRating, 5 stars1 week ago
For basics, it is very clean and comfortable with a well appointed kitchen, comfortable beds, and easy street parking. The space itself is remarkable. Patterned tin walls and ceilings, a triangular shape, nicely decorated, and the construction details from converting it to an apartment are all in keeping with the style. We loved it.
Guest favourite
Flat in Maywood
4.92 out of 5 average rating, 97 reviews

Cozy guest studio, great for couples!

JulianRating, 5 stars1 week ago
Great place . Very nice and responsive host. Great for couples. Great location
Top guest favourite
Flat in Chicago
4.99 out of 5 average rating, 155 reviews

Vibrant & Chic Apt On Quiet St in Andersonville

DianeRating, 5 stars1 week ago
Staying with Johana was a pleasure. The location was perfect, the house was cozy and clean. Highly recommend.
Guest favourite
Flat in Chicago
4.92 out of 5 average rating, 51 reviews

Montrose Gardens

AndrewRating, 5 stars1 week ago
Great location, walkable from Metra & CTA stations. Cozy space. Exactly what I needed
Superhost
Flat in Chicago
4.78 out of 5 average rating, 40 reviews

Spacious Haven Near Green Line, 20mins to Downtown

María CamilaRating, 5 stars1 month ago
The accommodation is just as it appears in the photos, very large and comfortable. We arrived a little late and the metro station area is not so nice, and a little alone, however, the area is very central, access to bus, supermarket. Highly recommended this place, we really liked it.
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 26 reviews

Lovely Garden Studio Apartment.

JessicaRating, 5 stars5 months ago
Kasey and her husband were awesome host!!They were kind & responsive! My friend and I come during a time in winter and Kasey was very quick to keep us warm! Although they do have a child it was very rare when we were disruptive by noise! Love the vibes of the Airbnb and the fact that I felt like home says something! I definitely recommend staying here. Such a co beautiful and peaceful area as well.

House rentals with a patio

Guest favourite
Home in Chicago
4.94 out of 5 average rating, 33 reviews

Modern Family Townhouse

DeliaRating, 5 stars2 months ago
Convenient to Hyde Park and the University of Chicago, the home was incredibly clean. I was a little worried since this is the hosts' primary home, but the kitchen was clutter-free, and the bedrooms had plenty of room for our personal items. It was also great to have a guaranteed parking spot in a gated area. The owner was proactively communicative, and everything was just as described. The rental easily fit our family of five. Would definitely stay here again!
Superhost
Home in Chicago
4.91 out of 5 average rating, 46 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

ChepeRating, 5 stars1 week ago
Very comfortable place and nice and very responsive host! Definitely recommend this stay!
Guest favourite
Home in Chicago
4.97 out of 5 average rating, 245 reviews

Division St Designer Home In Heart of Wicker Park

MatthewRating, 5 stars4 days 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
Home in Chicago
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, 152 reviews

Unique porcelain-enamel paneled "Lustron" home

MichelleRating, 5 stars1 week ago
We enjoyed our 2nd visit as much as the 1st. Great location! Wonderful hosts! Cool house! Comfortable beds! Beautiful serene backyard. (=
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 39 reviews

Floresitas Oasis, your home in Chicago

KevinRating, 5 stars2 weeks ago
Wonderful stay once again. Place is immaculate and very comfortable . Host is fast to respond with any messages as well. Would highly recommend
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 61 reviews

Private Logan Square Garden Apt

AthenaRating, 5 stars1 week ago
Had a lovely stay at Janice's place! It is located a short drive from Logan Square, which has restaurants, bars, and a blue line metro stop. There was also a bus stop just outside the neighborhood. Speaking of the neighborhood, it was very serene and private, with plenty of parking regardless of the time of day. The airbnb is a basement unit, so maybe something to keep in mind if you're on the taller side, but it was spacious, and there was minimal noise from the floor above. Shower had great water pressure! Bedroom was clean and comfortable. Janice was very communicative and clear instructions were given for checkin and checkout processes.
Top guest favourite
Home in Gary
4.96 out of 5 average rating, 89 reviews

Steps from the beach and a mile from National Park

PamelaRating, 5 stars1 week ago
>Loved the meticulous attention given to cleanliness and the Award Worthy Décor. >The apparent attention to detail and thought given to enhance comfort. >The Clear available directions and Immediate responsiveness to concerns regarding technical issues was unparalleled. > Wish I could've stayed longer! Absolutely Heavenly!!

Apartment rentals with a patio

Guest favourite
Apartment in Chicago
4.94 out of 5 average rating, 124 reviews

Urban Oasis | Great for Families w/ Kids

RichardRating, 5 stars2 weeks ago
Place was great. Clean and well laid out with plenty of room. Enjoyed our stay. Location was further than we thought from our places we planned to visit. They were cutting down and grinding a tree first thing Saturday morning. Convenient cafe right around corner had good breakfast food and coffee. Ubers were fast getting us and to where we needed to go. Parked car and left all weekend. Neighborhood was a little rough with homeless and panhandlers but they left us alone. Great walks to Soldier field and Northern Island. Alex provided all the amenities you need plus some Heinkens to cool us down. We had no issues so we did not need to contact Alex at all but yoyu got to remember the location is on 17 Place not Street so we almost walked into the wrong house and when the dog started barking at us we knew something was up. LOL!!!
Superhost
Apartment in Chicago
4.87 out of 5 average rating, 119 reviews

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

AlfredoRating, 5 stars1 week ago
Everything went well. Place was very nice and the host was very responsive when I needed help and accommodative as well. Highly recommend if needed a place near downtown.
Top guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 141 reviews

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

EvanRating, 5 stars1 week ago
I was coming to Chicago to just have a quiet weekend away from work and the stresses of home. I wanted a few days to enjoy urban life peacefully doing a few things I enjoy. This spot checked off all the boxes for peaceful and private but also re adorably we'll located to hit all of the spots around Chicago. The place was exactly as pictured and clean. couldn't have been easier and I would stay here again. hosts were responsive. it was a great few days.
Guest favourite
Apartment in Chicago
4.91 out of 5 average rating, 109 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

JonathanRating, 5 stars1 week ago
This was a fabulous place to stay! My brother and I could easily walk to the "L" and head downtown. The pizza place right downstairs was delicious - we ate there twice in three days! The beds were comfortable, the couch and living room set up was cozy. I would absolutely stay there again!
Superhost
Apartment in Chicago
4.86 out of 5 average rating, 152 reviews

Tri-Taylor/Medical Dist. near West Loop

JulioRating, 5 stars3 weeks ago
Great stay! The place was clean, comfortable, and in a convenient location. The host was friendly and helpful. I’d definitely stay here again!
Guest favourite
Apartment in Chicago
4.93 out of 5 average rating, 138 reviews

Modern Chicago Movie Themed Apt

LechelleRating, 5 stars2 days 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!
Top guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 165 reviews

Spacious 4 Bedroom Condo

ScottRating, 5 stars2 weeks 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.
Guest favourite
Apartment in Chicago
4.93 out of 5 average rating, 105 reviews

Wicker Park/Bucktown condo with large balcony

ErinRating, 5 stars1 month ago
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!

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