Vacation rentals with a patio in South Side

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Popular amenities for South Side 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
4.88 out of 5 average rating, 112 reviews

Lovely 2-bedroom apartment in Pilsen

BarboraRating, 5 stars1 week 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 favorite
A spacious bed with patterned bedding rests against a geometric accent wall painted in dark blue and vibrant yellow. Two nightstands with lamps are positioned on either side, contributing to the cozy and modern aesthetic of the room.
Apartment in Maywood
4.92 out of 5 average rating, 99 reviews

Cozy guest studio, great for couples!

BrittanyRating, 5 stars1 day ago
Lovely basement studio in very nice neighborhood. Easy drive to nearby neighborhoods or downtown area. Highly recommend if you’re looking for a comfortable stay!
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 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 favorite
A spacious living room is presented with a comfortable green sofa and two light-colored chairs. A large flat-screen TV is mounted on a wooden media console. A round coffee table sits in the center, surrounded by a soft area rug. Natural light filters through sheer window curtains.
Apartment in Chicago
4.8 out of 5 average rating, 10 reviews

3 Bed 3 Bath Lakefront Oasis, Parking Included

NathanRating, 5 stars4 days ago
Great stay. The property is tucked away and is away from all the city noise. It was very clean and everyone was really impressed. Thank you Sally for a great stay.
Guest favorite
A spacious living area features a modern sectional sofa in neutral tones. A sleek television is mounted on the wall opposite a minimalist coffee table. The adjoining dining area, visible through an archway, includes a round table with four chairs.
Apartment in Forest Park
4.87 out of 5 average rating, 255 reviews

Home in Forest Park Upstairs.

AmberRating, 5 stars5 days ago
He was available without delay and really seemed like a kind person. The location is wonderful whether you're looking for safe and simple stay or a trip into city. Highly recommend!
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, 301 reviews

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

MoniqueRating, 5 stars2 days ago
Only got to stay one night but it was a great hidden gem right outside the city! Needed a break from all the hustle and bustle. Had everything I needed, and the bed was so cozy! Christine and Dan always responded to me very quickly. Would stay again!
Guest favorite
A spacious basement entertainment area features a comfortable sectional sofa and a large coffee table. A pool table is positioned in the center, while a wall-mounted TV and an electric fireplace create a relaxed atmosphere. Light-colored walls and flooring enhance the space's openness.
Apartment in Chicago
4.86 out of 5 average rating, 109 reviews

Logan’s Cozy Inn.

SandraRating, 5 stars2 weeks ago
Great location with lots of nice bars and restaurants locally and easy access also to the CTA blue line to Downtown and O’Hare. Apartment was ideal and was just as described. Would recommend and if ever back in Chicago would look to stay here again.
Guest favorite
The cozy suite features a spacious bed with soft bedding, accompanied by a reading chair and ottoman. A small bookshelf holds various books, and two windows allow natural light to fill the room. A potted plant adds a touch of greenery to the decor.
Apartment 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

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
4.68 out of 5 average rating, 19 reviews

Lux_Home Chicago 8 mins Downtown

MicahRating, 5 stars1 week ago
I had a great experience staying at this Airbnb! The place was clean, cozy, and just as described in the listing. The host was very responsive and made check-in super easy. I’d definitely stay here again.
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 Chicago
4.97 out of 5 average rating, 246 reviews

Division St Designer Home In Heart of Wicker Park

MatthewRating, 5 stars1 week 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 modern kitchen features white cabinetry and sleek countertops. Stainless steel appliances including a refrigerator and dishwasher are visible. Natural light filters through the windows, illuminating the herringbone-patterned backsplash. An island offers additional prep space, with a wooden cutting board displayed on the countertop.
Home in Chicago
4.83 out of 5 average rating, 18 reviews

3BR Bungalow w/Bonus Room & Gym

AngelRating, 5 stars2 weeks ago
Keya was great host and was responsive with any questions we had! Great location and felt secure going in and out of home. Great amenities and was described well! Will definitely consider coming back and would recommend for any people considering. 10 out of 10 for me!!
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, 152 reviews

Unique porcelain-enamel paneled "Lustron" home

MichelleRating, 5 stars2 weeks ago
We enjoyed our 2nd visit as much as the 1st. Great location! Wonderful hosts! Cool house! Comfortable beds! Beautiful serene backyard. (=
Guest favorite
A modern kitchen features dark wood cabinetry paired with light granite countertops. Stainless steel appliances, including a refrigerator and oven, are enhanced by a stylish backsplash. A dining area with a square table and tall chairs is complemented by bar seating at the island.
Home in Chicago
4.95 out of 5 average rating, 40 reviews

Floresitas Oasis, your home in Chicago

KelvinRating, 5 stars4 days ago
Lizbeth’s place was a great stay! It was cozy, clean, and had more than enough space for me and my three friends. While it was a little farther from the city center than I initially expected, the neighborhood made up for it with tons of great restaurants nearby—there was always something good to eat just around the corner. Lizbeth was also a fantastic host—very friendly and super responsive whenever we had questions. Would definitely recommend her place to anyone visiting the area!
Guest favorite
A spacious sleeping area features a queen-size bed with layered white bedding and decorative pillows. Light fills the room from a nearby window, while a wooden dresser and nightstand provide storage. A textured stone wall adds visual interest to the overall decor.
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.
Guest favorite
A well-lit sleeping area is featuring two spacious beds with crisp white bedding. A dresser is positioned nearby, and a round mirror is mounted on the wall, reflecting natural light from a window. A bold blue accent wall adds a pop of color to the room.
Home in Oak Park
4.97 out of 5 average rating, 115 reviews

Garden Unit, King & Queen, Kitchenette & Parking

SarahRating, 5 stars1 week ago
We stayed one night and were very happy with the accommodations. Lisa was a helpful host and everything was very nice quality and squeaky clean. The bed was super comfortable and the shower was very nice with a big “rain” type showerhead AND a regular size detachable one. The neighborhood and yard area was calm and chickens were very cute! We had some fantastic empanadas at a nearby cafe called La Mulata - definitely recommend. There are a bunch of cool historical buildings nearby too (including the building the cafe is in). FYI since it’s a basement apartment (as advertised) there are a couple spots with slightly lower beams coming down from the ceiling). At 6’2” we were good to walk around without impediment, but I put my hand above my head at the lowest spot and the clearance was only about an inch, so if you are any taller, be careful or you may hit your head! Excellent place - thanks Lisa :)
Top guest favorite
An outdoor seating area features a wooden deck surrounded by green plants. Comfortable gray sofas are arranged around a central fire table, offering a cozy gathering space. A pergola provides partial shade, and hanging flower baskets add a splash of color to the environment.
Home in Chicago
5 out of 5 average rating, 9 reviews

Exquisite Chicago Modern Rooftop, Sleeps 9

GloriaRating, 5 stars5 days ago
I love everything about this home and all the e amenities, and the private rooftop was the greatest touch of the property Vince was amazing and very easy to reach in very fast responding.Thanks so much .

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 Chicago
4.96 out of 5 average rating, 114 reviews

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

J'HonnaRating, 5 stars1 week ago
The location was great. About 15 min from downtown. The place was beautiful and clean. I would definitely book with Julia again.
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
4.9 out of 5 average rating, 116 reviews

Convenient & Spacious 3BR Condo w/Free Parking

AlexisRating, 5 stars2 weeks ago
We enjoyed our stay at Yuyi’s. The space was very clean! There is a beautiful park across the street, delicious restaurants all around, and a grocery store 4 blocks away! We traveled in for business and it was perfect for us, Would love to stay again the next time we are in Chicago.
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 Chicago
4.94 out of 5 average rating, 125 reviews

Urban Oasis | Great for Families w/ Kids

MelissaRating, 5 stars1 day 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, 119 reviews

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

AlfredoRating, 5 stars2 weeks 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 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 Chicago
4.97 out of 5 average rating, 143 reviews

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

AnthonyRating, 5 stars2 days ago
This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.
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, 109 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

JonathanRating, 5 stars2 weeks 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!
Top guest favorite
A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.
Condo in Chicago
4.98 out of 5 average rating, 118 reviews

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

RebeccaRating, 5 stars1 week ago
One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!
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 Chicago
4.93 out of 5 average rating, 138 reviews

Modern Chicago Movie Themed Apt

LechelleRating, 5 stars6 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!

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