Vacation rentals with outdoor seating in Chicago

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Chicago outdoor seating rentals

House rentals with outdoor seating

Superhost
The rooftop terrace is furnished with a seating arrangement of four cushioned chairs surrounding a rectangular table. Soft outdoor lighting is provided by string lights above, enhancing the space. A panoramic view of the city skyline is visible in the background, showcasing an expansive horizon.
Home in Oak Park
4.8 out of 5 average rating, 85 reviews

Rooftop Access with Views and Gym - LCP Collection

AllisonRating, 5 stars1 month ago
Great location, clean, spacious, great linens and towels.
Top guest favorite
Home in Chicago
4.98 out of 5 average rating, 108 reviews

Flat in Lincoln Park 2-Flat Central to Everything

OlivierRating, 5 stars1 month ago
We stayed for a week with 2 children of 8 and 10. The place is larger than we expected; which is nice. The street and neighborhood are both really nice. Train is close; which is very handy to visit the city. Close to Lincoln park and many restaurants and shops. This place was very comfortable, private and quiet. Brian was also also very flexible with check in and check out times. Definitely recommended !
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 Ukrainian Village
4.92 out of 5 average rating, 49 reviews

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

ZafarRating, 5 stars1 month ago
Great stay and easily accommodated ng larger in laws family
Guest favorite
An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.
Home in Bridgeport
4.96 out of 5 average rating, 122 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

LuciaRating, 5 stars1 week ago
We were 4 adult and 1 dog and we stayed at Matthew's place, everything went smooth and easy to feel at home, parking spot and great location of the house make us everything easier, it was so fast to get to the downtonw in lees than 20 minutes. Matthew was always responsive to all our questions, I definitely will search for this place to sray on my next trip to chicago.
Superhost
A modern kitchen is characterized by dark wood cabinetry and stainless steel appliances. A spacious dining table is surrounded by four chairs. Natural light enters through a door, which leads to the outside, creating a bright and functional cooking space.
Home in Maywood
4.76 out of 5 average rating, 123 reviews

Maywood Relaxation

MadiRating, 5 stars5 days ago
We came for The Weeknd concert in the city, so we got ready there, then spent the night and morning in the house. It was a beautiful house and felt super peaceful and safe! The beds were insanely comfy and we all slept so well! So much space! Everything was just so homey and comfortable.
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 Humboldt Park
4.95 out of 5 average rating, 60 reviews

Private Logan Square Garden Apt

StephanieRating, 5 stars5 days ago
Janice’s listing was wonderful. Everything was as described and we thoroughly enjoyed our stay. We met Janice when we crossed paths the second night there and she was very friendly and great to talk to. We look forward to staying at Janice’s place next time we’re back in Chicago.
Top guest favorite
A row of multi-story brick buildings is presented along a tree-lined sidewalk. Each unit features large windows adorned with decorative elements. Soft illumination from the interiors creates a welcoming ambiance as greenery frames the entrance, and a secured fence borders the property.
Home in Lake View
4.98 out of 5 average rating, 256 reviews

Wrigleyville Southport Studio

KyleRating, 5 stars2 days ago
Great little hideaway to rest and recharge after being out in the city all day.
Guest favorite
A two-story brick home features a welcoming front porch with a stoop and entrance framed by tall windows. Lush greenery and vibrant flower beds add color to the exterior, enhancing the inviting presence of the residence.
Home in Dunning
4.95 out of 5 average rating, 19 reviews

Big house in the BEST Location!

AbhishekRating, 5 stars5 days ago
It was as pictured and suited our needs. Clean and well organized. When we reached out we were responded to promptly and thoroughly. The location is good and walkable. If planning to go to Navy Pier or the Miracle Mile to go shopping (or something in that general area of Chicago), expect about a 40 - 60 min drive.

Apartment rentals with outdoor seating

Top guest favorite
A well-lit bedroom features a spacious bed with a patterned duvet and decorative pillows. A small dining table with two chairs is positioned near the kitchenette, which includes a stove and refrigerator. Large windows allow natural light to fill the room, complemented by soft curtains.
Apartment in Ukrainian Village
4.9 out of 5 average rating, 524 reviews

iKlektik House Chicago / Robin

JarronRating, 5 stars2 weeks ago
Mindy & Tony’s place was a nice hidden gem. Their home was cozy and includes all you need for a stay in Chicago. There was plenty of street parking and the area is quiet. I would highly recommend for a solo traveler or couple.
Top guest favorite
The front room features a plush leather couch adorned with vibrant red throw blankets, complemented by a bold red and white area rug. Bright teal curtains frame the windows, allowing natural light to fill the space. A coffee table is placed centrally, surrounded by decorative plants and artwork.
Apartment in West Town
4.95 out of 5 average rating, 431 reviews

A Vintage Pink House in the Heart of Chicago

SharanRating, 5 stars6 days ago
Had an amazing stay! Felt right at home! Amazing supplies in the kitchen were a completely pleasant surprise! The location and the locality were also absolutely amazing and a very short drive from downtown Chicago.
Guest favorite
A cozy seating area is highlighted by a modern electric fireplace beneath a mounted television displaying streaming options. Soft cushions and a pastel throw blanket add comfort to the light-colored chair. A touch of decor is presented with wall art and a small side table.
Apartment in Oak Park
4.92 out of 5 average rating, 177 reviews

Lovely, spacious 2bd, 1bath home w/free parking

ChristinaRating, 5 stars3 days ago
Tiffany was friendly host and made sure to communicate with us to make our stay enjoyable. The place walkable distance to public transit and the neighborhood was safe enough to walk at night. It was clean and as pictured, there was coffee, utensils, plates, etc if you needed prepare food.
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, 155 reviews

Sunny 1 bedroom apartment 1 block from restaurants

AmeliaRating, 5 stars1 month ago
Jim’s place had all of the modern amenities you could want and than some. He had great books to read, and beautifully curated pieces of art throughout the home. We felt very comfortable and safe there.
Guest favorite
A bright kitchen area features a round table with a red and white checkered tablecloth and four white chairs. A small sink and a gas stove are present, along with a refrigerator. Natural light filters through a window adorned with a red gingham curtain.
Apartment in Berwyn
4.92 out of 5 average rating, 378 reviews

Private apartment with retro vibe

ErickRating, 5 stars1 week ago
Clean and peaceful neighborhood. Parking was not an issue
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, 106 reviews

Cheerful Oak Park Apartment

CholeenRating, 5 stars1 week ago
This place is a hidden gem- perfect price, for the perfect location for a nice weekend vacation get a-way! My boyfriend and I found the place to be clean and cozy! Thanks for having a beautiful home and letting us book with you!
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 Logan Square
4.86 out of 5 average rating, 109 reviews

Logan’s Cozy Inn.

SandraRating, 5 stars1 week 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 kitchen area features a modern design with wooden cabinetry and a sleek countertop. Four black bar stools are positioned at a counter, which faces an abundance of natural light from a window. The kitchen is equipped with new appliances and organized shelves for easy access.
Apartment in Chicago
4.98 out of 5 average rating, 403 reviews

Peaceful River West, free parking

JoeRating, 5 stars1 week ago
My wife and I visited Chicago and Mando's flat with another couple for Memorial Day weekend. The place was exactly as described and everything was clean and nice. Having stayed in quite a few downtown AirBnB's across the country, I was very pleasantly surprised by Mando's pre-arrival instructions and recommendations, those are truly the best and most descriptive ones I have ever received in my travels. Additionally, it was lovely that Mando provided us with snacks and a few drinks for our stay. I will definitely look to stay at this place again next time I return to Chicago with the right sized group.

Condo rentals with outdoor seating

Guest favorite
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 Pilsen
4.85 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 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 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!
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 Lake View
4.98 out of 5 average rating, 118 reviews

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

RebeccaRating, 5 stars5 days 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 Ukrainian Village
4.93 out of 5 average rating, 136 reviews

Modern Chicago Movie Themed Apt

IsaacRating, 5 stars6 days ago
The house was nicely situated, tidy, and perfect for our needs. They definitely keep to the movie theme, and I liked the little porch in the back.
Top 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 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 favorite
A spacious living area showcases a light-colored sofa paired with dark green accent chairs. A glass coffee table sits atop a patterned rug, while decorative elements, including candles and potted plants, are arranged on a wall shelf. Natural light enters through large windows.
Condo in Bucktown
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!
Guest favorite
A modern living area features a green sofa positioned in front of a glass coffee table on a patterned rug. An open kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light fills the space, enhancing its welcoming atmosphere.
Condo in Uptown
4.97 out of 5 average rating, 124 reviews

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen

SusanRating, 5 stars5 days ago
Pablo was an incredibly responsive and helpful host, even volunteering to have us check in early. His place was spacious (can accommodate 4-5 people) and comfortable. . . really a home away from home. Had everything we needed for a 5-day stay . . washer/dryer a plus! Parking can be a challenge, but using SPOT Hero helped us identify available spots. While next to the train, the train noise was more like white noise and did not disturb us. Would definitely stay again!
Guest favorite
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Little Italy
4.94 out of 5 average rating, 207 reviews

Private hot tub - King bed suite - Free parking

ZackRating, 5 stars2 weeks ago
Cody’s place was a perfect hideaway from which to venture into the city, and both far enough away to be peaceful but close enough to a string of good restaurants and cafes to be walkable. Check-in and house instructions were comprehensive, Cody himself was proactive and communicative, and the hot tub was a major plus on cool nights. Looking forward to another stay!

Quick stats about vacation rentals with outdoor seating in Chicago

  • Total rentals

    2.7K properties

  • Total number of reviews

    188K reviews

  • Family-friendly rentals

    1.8K properties are a good fit for families

  • Pet-friendly rentals

    920 properties allow pets

  • Rentals with a pool

    290 properties have a pool

  • Rentals with dedicated workspaces

    2.2K properties have a dedicated workspace

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