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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

Guest favorite
A spacious living area features a large sectional couch, adorned with decorative pillows. A sleek coffee table sits in front, and a framed cityscape photograph hangs on the wall. Natural light illuminates the space through three windows, enhancing the welcoming atmosphere.
Home in Roscoe Village
4.92 out of 5 average rating, 288 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

AlexanderRating, 5 stars1 week ago
What a lovely home! We and our two daughters had a great stay. The master bedroom is quite spacious, the beds are comfortable, there was ample closet space, and the kitchen is fantastic! The Roscoe Village neighborhood more generally is charming and walkable to any trips for essentials (multiple grocery stores and pharmacies within half a mile). While the Cubs were on the road during our trip, the house is an easy 20-minute walk to Wrigley Field. And Sharleen was always prompt and very helpful in answering the questions we had. We would happily return!
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 stars2 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 living area features a brown leather sofa accompanied by two accent chairs, all arranged around a glass-top coffee table. Natural light enters through a large window adorned with flowing curtains, complemented by a decorative mirror and wall-mounted storage.
Home in Lisle
4.93 out of 5 average rating, 135 reviews

Cozy House, Main Road Access, Close to Colleges

SarahRating, 5 stars3 weeks ago
Vic's place was a convenient place to relax in between graduation weekend events. Close to jumping onto any of the major roads to the city or other suburbs but also the town of Lisle has great restaurants right there. The home is right on a busy road but surprisingly quiet once you're inside. We had a few gorgeous spring days and were able to sit outside on the patio enjoying time with extended family which was a definite perk. Thanks, Vic!
Superhost
An open-concept living area features high wooden beams and a large flat-screen TV mounted on a dark accent wall. A stylish dining table accommodates six, while the kitchen showcases modern cabinetry and stainless steel appliances. Natural light fills the space through nearby windows.
Home in Illinois Medical District
4.87 out of 5 average rating, 106 reviews

Casa PLZN Location | Entire Home | Garage Parking

RachelRating, 5 stars3 weeks ago
We had a wonderful stay. The place was clean, comfortable, and had enough space for our larger group. It was really nice getting to use the garage parking space and the outdoor area is cozy. After day 1, we did have trouble getting into the place through the front door keypad, there was a battery issue. Thankfully there is access to the home through the back door/garage. Thanks for a great stay!
Guest favorite
Home in Avondale
4.94 out of 5 average rating, 147 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

MaitlandRating, 5 stars1 week ago
My family and I had a fantastic stay! The space was exactly as described; clean, stylish, and thoughtfully designed. Check-in was smooth, and Adam was super helpful throughout our visit. We especially appreciated the backyard for our dogs . The location was perfect. It was close to everything we needed but still quiet and peaceful. Would absolutely stay here again and highly recommend to anyone visiting the area!
Top guest favorite
A bright living area is filled with comfortable seating, including two armchairs and a spacious sofa. A light area rug with a geometric pattern covers the floor. Natural light streams in through large windows adorned with wooden blinds, and a decorative tray sits on a plush ottoman.
Home in Lombard
5 out of 5 average rating, 28 reviews

Spacious Home in Chicago Suburbs

RoseRating, 5 stars1 month ago
This was a great spot for our larger group to stay during our visit to Chicago! Many places to eat nearby and spacious enough for everyone. The spit floor plan was also great as it gave our group different common areas to hang out in as well! The host was very accommodating for a late check out as well! Would certainly stay again!
Superhost
A comfortably arranged living room features a gray sofa with multiple cushions and two teal accent chairs. Natural light enters through large windows dressed in light curtains, while a wooden floor adds warmth to the space. A flat-screen TV is mounted on the white wall.
Home in Markham
4.73 out of 5 average rating, 124 reviews

The Country Life! Entire House.

DeniseRating, 5 stars2 months ago
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.
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
4.92 out of 5 average rating, 137 reviews

Quiet cul-de-sac with huge fenced in backyard

AshleyRating, 5 stars4 days ago
A great spot!! A friend and I were in town for a concert and this place was perfect! The patio was really cool and Tom has the cutest dog!!

Apartment rentals with outdoor seating

Superhost
The exterior of a historic Greystone building showcases a well-maintained facade, featuring large windows and ornate wooden doors. A flowering tree adds a touch of nature, while a wrought-iron gate frames the entrance, emphasizing the property's charm and welcoming atmosphere.
Apartment in Near West Side
4.82 out of 5 average rating, 282 reviews

The Banksy-Greystone Rooftop Firepit United Center

KrishRating, 5 stars2 weeks ago
I really enjoyed my stay at the Banksy.
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.
Guest favorite
A private rooftop patio is displayed, featuring a seating area with bright orange cushions on a dark wicker couch. A glass table is centrally placed, surrounded by panoramic views of the Chicago skyline under a partly cloudy sky.
Apartment in Near North Side
4.91 out of 5 average rating, 141 reviews

Modern 3BR with Private Rooftop & Free Parking

JaneRating, 5 stars3 weeks ago
It was very clean and comfortable beds/beddings. Great for a few night stay with family.
Guest favorite
A cozy living area features a modern black sectional sofa adorned with colorful throw pillows. A large photograph of a city skyline hangs on the wall. A small coffee table rests on a patterned rug, while a desk and chair are positioned beside a plant and shelves.
Apartment in Avondale
4.97 out of 5 average rating, 109 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

JoseRating, 5 stars2 weeks ago
10/10 - already booked again for a second trip
Guest favorite
An elevated outdoor space features multiple levels, including an upper deck with railing. Lush greenery and carefully arranged seating areas create an inviting atmosphere. The exterior of the structure is painted in soft hues, and large windows allow for ample natural light.
Apartment in Logan Square
4.98 out of 5 average rating, 99 reviews

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

KeithRating, 5 stars3 weeks ago
Super great living area and the outside patios were awesome. Really liked the inside sitting areas looking out over patio as well. Easy to find a quiet spot from family🤭
Guest favorite
A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.
Apartment in Evanston
4.82 out of 5 average rating, 181 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

NicholasRating, 5 stars1 month ago
The living room was very comfortable and provided a great space for all our group to hangout after a wedding. The extra bedding and coffee was a nice plus!
Superhost
Apartment in Chicago
4.84 out of 5 average rating, 100 reviews

Charming retreat w/ fireplace

RicardoRating, 5 stars3 weeks ago
Me And my fiancée had a great time, clean place, and worth every cent, only downside is parking.
Superhost
An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.
Apartment in East Rogers Park
4.9 out of 5 average rating, 173 reviews

Executive Apartment on Lake Michigan with parking

FrankRating, 5 stars1 week ago
No problem except for us French to find out how the cooking utensils work and in particular the hood, a manual would be good, too bad for the bad weather the exteriors would have deserved to be used but the weather is not part of the package

Condo rentals with outdoor seating

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 Bridgeport
4.9 out of 5 average rating, 115 reviews

Convenient & Spacious 3BR Condo w/Free Parking

MichelleRating, 5 stars2 weeks ago
Loved this condo. We had 7 adults staying and felt comfortable. Having a dedicated parking space was super helpful and on street parking was easy. Please note this is a 3rd floor walk up so if stairs are a problem you need to consider if this works for you. Easy access to Midway airport and Chinatown were also great features.
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 Pilsen Historic District
4.93 out of 5 average rating, 123 reviews

Urban Oasis | Great for Families w/ Kids

RichardRating, 5 stars1 week 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!!!
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 Lincoln Park
4.91 out of 5 average rating, 109 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

JonathanRating, 5 stars5 days 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!
Guest favorite
A bedroom features a spacious bed with neatly stacked towels at its foot. A mural depicting a baseball player stands on one wall, complemented by a nearby mirror and door. The room is designed with light wood flooring and sports-themed decor.
Condo in Wrigleyville
4.84 out of 5 average rating, 431 reviews

Authentic Condo steps from Wrigley Field!

KellyRating, 5 stars2 weeks ago
Absolutely loved this apartment! You can not have a better location in Wrigleyville. My only “bad” feedback was the neighbors. Can you really smoke weed all day long?
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 stars2 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!
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 is arranged with a large sectional sofa facing a wall-mounted television. A decorative area rug lies beneath a low coffee table. Adjacent, a dining area features a wooden table surrounded by chairs, with an open kitchen visible in the background.
Condo in River North
4.99 out of 5 average rating, 137 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

MohamedRating, 5 stars3 weeks ago
Great responsive host. The place was clean and check in was easy. They were very responsive and accommodating. The location was excellent and easy to navigate with plenty to do within walking distance.
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 Logan Square
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!

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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