Vacation rentals with outdoor seating in West Loop, Chicago

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for West Loop, Chicago outdoor seating rentals

House rentals with outdoor seating

Guest favorite
The spacious backyard features a covered dining area with a large table and chairs, adjacent to a comfortable seating area under a pergola. A grilling station is included, surrounded by decorative landscaping and privacy fencing.
Home in Brookfield
4.92 out of 5 average rating, 87 reviews

Remodeled | Game room | Fire Pit | 5 Min to Zoo

KateRating, 5 stars3 days ago
Best Airbnb we’ve stayed at yet! Thanks to Giovanni we were able to visit with our family for Easter. The previous Airbnb we booked cancelled on us at the last minute; hours before we were set to arrive in Chicago from Detroit. The space was just like the pictures. It was clean and we felt right at home. The backyard was spacious and is fenced.
Guest favorite
The exterior of a modern brick home is showcased, featuring large windows and a welcoming entrance. A patio area includes a table with six chairs and a gas grill, set against a backdrop of a well-maintained lawn.
Home in Bridgeport
4.96 out of 5 average rating, 117 reviews

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

AnneRating, 5 stars5 days ago
Matt was a wonderful host and very responsive. The house was exactly as described. It felt like a home away from home. Everything you need is provided for you. I was traveling with my teen sons and we enjoyed the hot tub each night and watched a movie while soaking and relaxing. The house is on the Southside of the city and which was a nice break from the buzz of downtown. The train is about a 20-25 minute walk and the White Sox stadium is right near there. I definitely recommend this place if you’re looking for a home in Chicago.
Guest favorite
A well-lit entryway showcases a wooden staircase with elegant railing leading to upper levels. The dark front door contrasts with the light walls, while a stylish cabinet and framed photos add character to the space, inviting guests into the home.
Home in Roscoe Village
4.92 out of 5 average rating, 280 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

BrigidRating, 5 stars2 weeks ago
We enjoyed preparing pizzas from scratch in the perfectly sized kitchen with our adult kids who live in Chicago and their friends. There was plenty of space to sit around the spacious kitchen island and talk while cooking. The whole experience was made even better by using the Wolf stove top and Bosch wall-mount oven, which produced perfectly crisp crust and tasty toppings. The neighborhood felt safe and peaceful while providing everything we needed within walking distance. Parking was also easy. We had no trouble finding a space in front of the house all 4 days we were there. As a special bonus, a new chocolate cafe opened a few days ago (Hotel Chocolat Velvetiser Cafe) and is just a short walk away! We had a great time in this lovely home.
Superhost
A bright living space features an orange sectional sofa adorned with decorative cushions. Colorful wall art creates visual interest, while a small kitchenette with a bar height table and stools is visible. Natural light filters in through large windows, complementing the warm wood floors.
Home in Bridgeport
4.71 out of 5 average rating, 51 reviews

Animal House near Sox stadium

AnneRating, 5 stars3 days ago
We had a great stay at Miranda's. The apartment was just as advertised and had lots of items to use in the kitchen. Miranda gave great restaurant recommendations. We loved the maple lattes at Blind Owl and had an excellent dinner at TLP (Three Little Pigs). Bridgeport is a quiet neighborhood with easy access to downtown Chicago. If you are traveling with a pet this is the place to stay, I felt guilty I left my fur baby at home.
Superhost
A small outdoor space features two blue chairs positioned on a light-colored area rug, surrounded by textured brick walls. Green vines adorn the wall on one side, adding a touch of nature. A white door provides access to the interior.
Home in Illinois Medical District
4.86 out of 5 average rating, 99 reviews

Casa PLZN Location | Entire Home | Garage Parking

CecilioRating, 5 stars3 weeks ago
Great place near restaurants and cafes. Garage access is a plus. Train noise is noticeable at first but you get used to it and it's only noise as the house doesn't rumble when the train passes.
Guest favorite
Home in Logan Square
4.95 out of 5 average rating, 38 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars6 months ago
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.
Top guest favorite
A modern living area is equipped with a wall-mounted television and a neutral sofa. A decorative coffee table and warm-colored accent chairs are positioned around the space. The room includes lush potted plants and framed artwork on the walls, enhancing the aesthetic appeal.
Home in Worth
5 out of 5 average rating, 16 reviews

3 x Queen Beds + Pull Out Sofa Bed - No Stairs !

SawsanRating, 5 stars3 weeks ago
Amazing house and location. Great host. Highly recommend.
Guest favorite
Home in Avondale
4.94 out of 5 average rating, 139 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

KendraRating, 5 stars3 weeks ago
Amazing spot - love the home and backyard area, and such a good peice point!! Short ride on the L downtown, safe home, and LOVE having access to a garage!! Adam was responsive and helpful, and he was so understanding about one of our kids who accidentally broke part of the furniture there. 5/5, would go back next time we are in Chicago!!

Apartment rentals with outdoor seating

Guest favorite
A private rooftop deck is illuminated by string lights, creating a warm ambiance. The wooden surface showcases a dining table surrounded by four chairs. The surrounding wooden railing offers a sense of privacy, while the nearby brick wall adds texture to the space.
Apartment in West Town
4.96 out of 5 average rating, 135 reviews

Bohemian Moto Inn

AllisonRating, 5 stars4 days ago
Great place to stay, just the right amount of space for two couples and really well located for exploring the neighborhood. We particularly enjoyed the large deck, very nice in good weather!
Superhost
An inviting dining area features a simple wooden table accompanied by two benches and a chair. A cozy seating arrangement includes a sofa and coffee table, framed by large windows dressed in light curtains. A ceiling fan and decorative accents add to the space.
Apartment in Lincoln Park
4.72 out of 5 average rating, 117 reviews

The Biddle House (#1)

SitaRating, 5 stars3 months ago
We really enjoyed staying at this place - it was clean and comfortable, and the location is fantastic. Elizabeth was very responsive and a great host. We would stay here again!
Guest favorite
A modern living space features a dark sofa adorned with colorful cushions. A round coffee table sits in front, accompanied by a small side table with a decorative vase. A large mirror reflects the cozy atmosphere, while a vibrant city skyline artwork adds visual interest to the wall.
Apartment in Avondale
4.97 out of 5 average rating, 106 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

JillRating, 5 stars1 month ago
Good location and had everything we needed. Handy to have nearby stores within walking distance. Great place and would definitely stay again.
Superhost
A spacious outdoor terrace is shown, featuring comfortable seating arrangements with orange cushions and a circular table. Potted greenery lines the space, and decorative string lights enhance the ambiance. A neutral rug adds warmth to the seating areas, inviting relaxation.
Apartment in East Rogers Park
4.89 out of 5 average rating, 166 reviews

Executive Apartment on Lake Michigan with parking

DebraRating, 5 stars1 month ago
This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!
Guest favorite
A two-story gray house with wooden siding is set amid trees. Stairs lead to a white front porch, and large windows allow for natural light. A lawn stretches along the side, offering a green space for outdoor enjoyment.
Apartment in Forest Park
4.84 out of 5 average rating, 179 reviews

Cozy & Convenient Oak Park w Parking / Transit

BillRating, 5 stars3 months ago
Elizabeth’s unit is cozy and quaint and has anything one could need. Bed is comfortable, shower is strong, kitchen is functional, and there is a small workspace for those in town for their job. A 15 minute walk to public transportation to downtown and elsewhere and there are two areas for restaurants, one just a 10 minutes walk. There is a small back porch for use in nicer weather and a dedicated parking space. Elizabeth is always available for questions and take pride in her rental. You won’t be disappointed.
Top guest favorite
A living area is highlighted by two leather sofas and a coffee table. A decorative fireplace features tiles in blue and yellow. A television is mounted above the fireplace, while a dining area is observed in the background, enhancing the spacious layout.
Apartment in Lake View
5 out of 5 average rating, 112 reviews

Spacious 2 Bedroom in the heart of Lakeview!

AlanRating, 5 stars2 weeks ago
Great location. Plenty of space. Responsive host. We hope to return in the future.
Top guest favorite
The living area features a comfortable sofa, paired with two woven armchairs. A rustic wooden coffee table sits at the center, adorned with a vase of fresh flowers. Natural light illuminates the space through two large windows, framed by soft curtains.
Apartment in Forest Park
4.99 out of 5 average rating, 346 reviews

Walk to Oak Park from Our Sunny Turn of the Century Apt

LindseyRating, 5 stars1 week ago
Beautiful clean home in a quiet neighborhood. It was perfect for our family and the hosts were helpful and hospitable. When we return to Chicago in the future we know we have a perfect place to stay!! 😊
Top guest favorite
A bright living room is highlighted by large windows that invite natural light. A comfortable brown leather sofa and a beige loveseat are positioned around a colorful area rug. A wooden coffee table and a wall-mounted TV complement the inviting space.
Apartment in Roscoe Village
4.97 out of 5 average rating, 145 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

GaryRating, 5 stars1 week ago
We really enjoyed our stay! We really like Roscoe Village and this apartment was perfectly located. Close to shops, coffee and restaurants. The check in process was easy and the apartment was well appointed with everything we needed. Parking was very easy as well. This was a great find for us and we will plan to visit again!

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
4.89 out of 5 average rating, 111 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars1 week ago
Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend
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 West Town
4.92 out of 5 average rating, 113 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

SearaRating, 5 stars1 week ago
Great place to stay! Quiet neighborhood and walkable distance from a few shops and food places. We enjoyed our stay very much!!
Guest favorite
A modern kitchen features sleek white cabinetry and a spacious island with four orange bar stools. A stainless steel refrigerator and cooking range are visible, while soft overhead lighting enhances the contemporary design. A TV is mounted on the wall, providing entertainment options.
Condo in Pilsen Historic District
4.93 out of 5 average rating, 117 reviews

Urban Oasis | Great for Families w/ Kids

ParkerRating, 5 stars1 week ago
We had a very good stay for a friends wedding a few blocks away in Chicago. As it is very modern, cozy, and clean. Alex's response time is very quick to whatever may arise. We would highly recommend staying there. Thanks for the stay!
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, 100 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

KendraRating, 5 stars3 months ago
John’s place was clean and cozy. The kitchen was immaculate and we appreciated the nespresso machine and pods. The location was excellent, many food and drink choices right outside the door. It was amazing to have our own parking spot! There are a lot of stairs but that is expected in the city. I would definitely recommend this spot to my friends.
Guest favorite
Condo in Wrigleyville
4.84 out of 5 average rating, 428 reviews

Authentic Condo steps from Wrigley Field!

SusanRating, 5 stars3 days ago
Great location. Accommodation just as described-fun decor. Comfortable beds.
Top guest favorite
An expansive street view patio features a railing and several seating options, including black chairs and a glass-top table. The view encompasses vibrant neighborhood storefronts and greenery, offering a glimpse of city life.
Condo in Lake View
4.98 out of 5 average rating, 115 reviews

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

TylerRating, 5 stars2 weeks ago
This is my favorite place to stay in all of Chicago! I try to come up 1-2 times a year and checking to make sure this spot is available is the first thing I do when planning out my trip(s). The apartment is spacious, comfortable, and clean; central to a lot of fun neighborhoods, and right above (and across) from some of the best nightlife in the city. Allan is an awesome host, always available if something’s needed, and super communicative. I’m already looking forward to my next visit so I can stay here again!
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, 160 reviews

Spacious 4 Bedroom Condo

IzabelRating, 5 stars1 week ago
Had a great time with friends and we were all able to comfortably hang out in communal spaces, get around the city. The bathroom to room ratio was ideal for a group of girls to get ready and the neighborhood made us feel safe walking around at all times of the day. Would recommend
Guest favorite
An outdoor patio space is showcased, featuring a large table surrounded by several chairs. String lights hang overhead, illuminating the area. A gas grill is positioned nearby against a backdrop of exposed brick and wood fencing, creating a secluded atmosphere.
Condo in River North
4.98 out of 5 average rating, 132 reviews

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

DavidRating, 5 stars1 week ago
One of the best airbnbs I’ve ever stayed at. Great condo, great location, and super responsive hosts. Highly recommend!

Quick stats about vacation rentals with outdoor seating in West Loop, Chicago

  • Total rentals

    160 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    6.7K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with a pool

    100 properties have a pool

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