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
4.86 out of 5 average rating, 113 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 stars3 days 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!
Superhost
A private patio features a fire pit surrounded by comfortable seating, providing a relaxing outdoor space. The skyline view showcases urban architecture, adding to the metropolitan ambiance. The arrangement encourages gatherings, while the fire pit enhances the inviting environment.
Apartment in Chicago
4.77 out of 5 average rating, 102 reviews

McCormick 2B/2Ba for up to 6 guests/private Patio

LouRating, 5 stars1 month ago
Good place to stay, I would definitely stay here again. This place has a security guard downstairs so it feels safe. The unit was clean and easy to get around the city.
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 stars6 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 stars1 week 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, 302 reviews

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

MoniqueRating, 5 stars4 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!
Top guest favorite
A serene bedroom displays a comfortable bed adorned with soft, neutral linens and plush throw pillows in warm tones. Two bedside tables hold lamps, providing gentle light. A textured wall art piece hangs above the bed, contributing to the calming ambiance of the space.
Apartment in Oak Park
5 out of 5 average rating, 14 reviews

Loft on Lake in Oak Park

RonRating, 5 stars1 week ago
Super stay! Everything was great. Bathrooms are modern and well-designed. The deck outside the back door was spacious and a great amenity. What a treat to stay there!
Guest favorite
The living area features a large gray sofa, a stylish armchair, and a modern media console with a television. Natural light filters through two large windows, providing a view of the surroundings. A small plant and decorative rug add subtle touches to the space.
Apartment in Chicago
4.98 out of 5 average rating, 107 reviews

Millennium park 10 min Free P-Spot&Balcony Sleep 8

BobbyRating, 5 stars2 weeks ago
Serg is an amazing host and his team for maintenance was extremely responsive. The area was close to Chicago and clearly undergoing gentrification but across the street from a firehouse which surprisingly was not loud at night or during the day. Great rooftop views and the apartment itself was spotless and magnificent. While not many high end restaurants due to being 5 minutes outside of the city. Great stay and great value.

House rentals with a patio

Superhost
A spacious living area features a large sectional sofa adorned with colorful throw pillows. Sunlight streams through multiple windows, illuminating a light-colored rug. A ceiling fan is positioned above, and a modern television mounted on the wall complements the neutral tones.
Home in Chicago
4.92 out of 5 average rating, 48 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

EhjayRating, 5 stars1 week ago
Very nice space to bring friends over
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!
Guest favorite
The open living area features hardwood floors and a modern design. A large sectional sofa invites relaxation, while a dining space with a sleek table is visible in the background. Decorative light fixtures hang from the ceiling, enhancing the contemporary ambiance, and a staircase leads to the upper level.
Home in Chicago
4.92 out of 5 average rating, 51 reviews

Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

MohannadRating, 5 stars1 week ago
the house looked better than the pictures and the house was bigger than expected the heated floors were a great luxury I'd recommend to stay here but also recommend the owners 1 thing 1 the toilets need to be changed u have to wait like 5 mins in-between flushes they were very low pressured got irritating also the basement had a flood under the carpets near the pool table which made me not play pool bc I was standing in a soaked carpet which is an easy fix for future guest I'd recommend staying here if u want to be close to the city but not be in the heart of it and want to have easy parking n access to ur car
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, 42 reviews

Floresitas Oasis, your home in Chicago

KelvinRating, 5 stars6 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, 63 reviews

Private Logan Square Garden Apt

TiffanyRating, 5 stars1 day ago
Was a very nice and relaxing place to stay after spending time in the city! Really close to multiple bus stops which made the public transport really easy to access. The inside was very clean and nice, the bed is extremely comfortable! Would stay again!
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 stars1 week 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 .
Top guest favorite
A cozy living room features a gray sofa with decorative pillows, a round dining table with chairs, and a stone fireplace. Natural light enters through windows adorned with decorative molding, while a few bookshelves provide a space for books and decor. A colorful area rug adds warmth to the hardwood floor.
Home in Oak Park
4.98 out of 5 average rating, 161 reviews

Clean, Cozy 1st Floor Flat, Kitchen, Parking

PariRating, 5 stars2 weeks ago
This was our second time staying here, and everything was as comfortable as the first time. We highly recommend this place.

Condo rentals with a patio

Superhost
A modern living area is presented with large windows allowing ample natural light. A navy sofa sits beside a decorative coffee table on a patterned rug, with a stylish mirror and television mounted on the wall. The space features sleek wooden accents for a contemporary feel.
Condo in Chicago
4.84 out of 5 average rating, 134 reviews

816 PLZN Luxury Apt | Rooftop | Garage Parking

HasimeRating, 5 stars1 month ago
The host and team were very communicative. The space was beautiful with high ceilings , clean, spacious, and well equipped.
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, 115 reviews

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

EdwardRating, 5 stars4 days ago
When we were first looking for a place to stay, none of the available AirB&Bs looked great. A week later, we looked again, and suddenly Julia's place popped up. It was so much better looking, and with a fairer price, than any others I could find in the list. A two-bedroom that is a *real* two-bedroom, for the price that others were charging for a pull-out bed in the living room. It was just as beautiful in-person. We felt immediately at-home and comfortable. I'm someone who has insomnia, especially while traveling, but there, I had no problem sleeping somehow. Also, it truly is a short walk to the Blue Line, or even a just few steps from the 77 bus route, which goes to the Blue Line, or all the way right into downtown Chicago.
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 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, 120 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

RachaelRating, 5 stars1 week ago
Our stay was fantastic. We have three children and everyone was comfortable. The location was perfect, the hosts were clear communicators and quick to respond. We would stay here again in a heartbeat.
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 stars3 days 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, 144 reviews

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

AnthonyRating, 5 stars4 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, 110 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

NicolasRating, 5 stars3 days 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.

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