Vacation rentals with outdoor seating in West Side

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for West Side outdoor seating rentals

House rentals with outdoor seating

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 stars2 weeks 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
Guest favorite
An outdoor area features a partially enclosed space highlighted by warm wood paneling and a large window. A grill is positioned against the wall, with a concrete floor leading toward a well-lit interior visible through glass doors.
Home in Chicago
4.96 out of 5 average rating, 174 reviews

Chicago River House -BBQ Oasis now open!

ThomasRating, 5 stars1 week ago
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!
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
4.93 out of 5 average rating, 44 reviews

Floresitas Oasis, your home in Chicago

Kawina RochelleRating, 5 starstoday
Lizbeth was an amazing host. She’s responsive and attentive. The place was exceptional clean and had an amazing smell. I was there to celebrate my birthday and was pleasantly surprised upon entry when I was greeted with a personalized birthday message, fresh flowers and a bottle of wine. Anytime I reached out to Lizbeth, she responded expeditiously. Again, very attentive. My husband and I will definitely stay at her beautiful Oasis again. We felt comfortable and completely safe. Everything we wanted to do was a quick drive from the location. If you’re considering staying at her home, you will not regret it. If I could give more than 5 stars, I would. Thanks Lizbeth for being an incredible host Until the next time…
Top guest favorite
A cozy living space features a grey sectional sofa adorned with a decorative pillow. A colorful area rug adds warmth, while a staircase leads to the upper level. Natural light streams through large windows, highlighting framed artwork and a plant positioned near a wooden cabinet.
Home in Chicago
5 out of 5 average rating, 26 reviews

Sunny Historic Cottage on the Park

MichelleRating, 5 stars6 months ago
We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.
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 week 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!
Guest favorite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island serves as a dining space, complemented by two navy blue stools with gold accents. Pendant lights provide illumination, enhancing the contemporary feel of the room.
Home in Chicago
4.86 out of 5 average rating, 139 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

ShaniaRating, 5 stars2 weeks ago
I enjoyed my stay. It was clean and pleasant. Marilyn was very friendly and quick to respond to any questions I had. I would recommend staying at this Airbnb! Great time!
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, 164 reviews

Clean, Cozy 1st Floor Flat, Kitchen, Parking

NathanielRating, 5 stars4 days ago
Great get away especially anyone in the architectural field. Great location in the suburbs of Chicago and has a great connecting train station near by that takes you into the heart of Chicago. Overall great stay!
Superhost
A landscaped outdoor space features a stone path leading through patches of green grass. Various planters display blooming flowers, while a cozy seating area is situated on one side. Wooden stairs ascend to the upper level of the building, surrounded by trees and shrubs.
Home in Chicago
4.93 out of 5 average rating, 107 reviews

Beautiful Chicago Greystone

RoxanaRating, 5 stars2 weeks ago
Great place to accommodate a big group. Close enough to the city if you don’t want to be in the heart of the city. Responsive host

Apartment rentals with outdoor seating

Guest favorite
A dining area is highlighted by a round table adorned with a lace tablecloth and a small vase of flowers. Light filters through large windows, illuminating the wooden floor. Adjacent, a living space features a couch, chairs, and decorative pieces that create a welcoming environment.
Apartment in Chicago
4.96 out of 5 average rating, 298 reviews

Logan Square 2nd Floor Chicago Victorian

JaspreetRating, 5 stars3 weeks ago
We had an amazing stay at Kitty’s place! From the moment we arrived, she made us feel so welcome. She even decorated the house for my fiancée’s birthday and left us treats, which was such a sweet touch. Her recommendations were super helpful and made our trip even better. The house was full of books and art that made it feel really special, and the beds were super comfy. The separate entrance was great for privacy, and street parking was easy to find, which was a big plus. Thank you so much for all the little things that made our stay unforgettable. We would love to stay here again very soon!
Superhost
A modern kitchen area with an island and bar stools is shown, adjacent to a dining space with chic seating. A bright living area features a PAC-MAN arcade machine. The bathroom is visible, showcasing contemporary fixtures and a clean design. All spaces exude a cozy ambiance.
Apartment in Chicago
4.9 out of 5 average rating, 163 reviews

Cozy Luxurious Beauty - 10 Min to Downtown Chicago

AaronRating, 5 stars1 week ago
Freddie was a great host. He responded right away when I had a little confusion & smoothed everything. The inside was beautiful & created a comfortable space to return after being out and about.
Guest favorite
A sunlit bedroom features a Queen-sized bed with crisp white linens and a plush headboard. Large windows framed by patterned curtains provide a view, while hardwood floors add warmth to the space. A striped area rug complements the decor, creating a cozy atmosphere.
Apartment in Chicago
4.97 out of 5 average rating, 175 reviews

Great Location & Bright 2BR+2BA | Mapletree Suites

CyndieRating, 5 stars4 days ago
Loved the area! Super close to restaurants and where our daughter lives do it was a great location
Guest favorite
A modern living area showcases a comfortable gray sofa with decorative pillows. A sleek coffee table is positioned in front of the sofa, accompanied by a small bowl holding a plant. Bright natural light filters through large windows, highlighting the contemporary design.
Apartment in Chicago
4.86 out of 5 average rating, 113 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

DeniseRating, 5 stars3 weeks ago
I loved everything about my stay ! Very nice and clean and the host were amazing
Guest favorite
A modern kitchen features stainless steel appliances including a gas stove, microwave, and refrigerator. White cabinetry complements the light countertops. Natural light enters through a window above the sink. A small area rug adds warmth to the hardwood floor, with a dining table visible in the background.
Apartment in Chicago
4.75 out of 5 average rating, 508 reviews

Sun filled tranquil 2 br great part of Logan Sq.

NaomiRating, 5 stars5 days ago
This was a very nice stay. It was super clean and in a great neighborhood. Thank you for hosting!
Superhost
A modern living area features a green sectional sofa, complemented by decorative pillows and a round coffee table. Exposed wooden beams and industrial-style ductwork are visible on the ceiling. A small window allows natural light, highlighting the textured gray walls and wooden flooring.
Apartment in Chicago
4.85 out of 5 average rating, 104 reviews

Charming retreat w/ fireplace

LoreleiRating, 5 stars1 week ago
This place was amazing!! Felt right at home as soon as we got there. The neighborhood is very quiet and chill, there’s a ton of great mexican food/stores, and just a couple blocks from the pink line and bus stop. Great home base just outside of the chaos of downtown but easy to get anywhere you wanna go! The place itself was comfortable and felt very roomy. Only thing is there are some upstairs neighbors who you WILL hear walk, talk, breathe… but we didn’t have trouble dealing with it and still slept well. Plus they had two cute little doggies who came to say hi, which is a huge plus! Overall 10/10 would stay again and would always recommend to anyone visiting Chicago.
Top guest favorite
The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.
Apartment in Chicago
4.98 out of 5 average rating, 119 reviews

Belmont Pleasures - hot tub / arcade gaming room

AustinRating, 5 stars5 days ago
Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.
Top guest favorite
A cozy seating area features a round table surrounded by two chairs. A potted plant is positioned nearby, contributing to the fresh atmosphere. A glass coffee table rests on a patterned rug, while a comfortable gray sofa with assorted cushions is present against the wall.
Apartment in Chicago
4.98 out of 5 average rating, 283 reviews

Ukrainian Village Garden Retreat

MercedesRating, 5 stars3 weeks ago
Marc’s place was exactly as listed. The cleanliness was amazing. Not one speck of dust in sight. We thought the place was really cute. Was walkable to a few restaurants and cafe’s in the area. Street parking was available but we opted to use the garage since we didn’t drive our vehicle much. The garage was clean and secure and is a shared space with 2 other vehicles (I’m guessing the owner uses the other spots). This is a downstairs unit so you may hear people upstairs but nothing that was bothersome whatsoever. This place was perfect for what we needed during our 4 day stay. Would definitely come back again.

Condo rentals with outdoor seating

Guest favorite
A bright living area features large windows that allow natural light to fill the space. A modern green sofa is complemented by two matching chairs. A round wooden coffee table sits on a plush area rug, with decorative wall art adding character to the yellow-painted walls.
Condo in Chicago
4.86 out of 5 average rating, 153 reviews

Luxe 2BR Cozy Suite | Skyline Views near McCormick

OommenRating, 5 stars1 month ago
Milan runs a professional Airbnb service and promptly responded to all our queries. We stayed at Apartment No. 605 which, was clean and had all the required amenities for a comfortable stay.
Guest favorite
A light blue bedroom features a spacious bed with a soft white blanket and an orange throw. A mirror and air conditioning unit are positioned nearby, while two windows allow natural light to brighten the room. Art pieces decorate the walls, enhancing the inviting space.
Condo in Chicago
4.94 out of 5 average rating, 180 reviews

3 BR Summer GetAway, 15mins to Loop+Gated Parking

ThaddeusRating, 5 starstoday
Close to the green line for easy transportation.
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, 146 reviews

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

MichaelRating, 5 stars5 days ago
Great place! Everything was clean, in a good location and they communicated well.
Superhost
A living area features a leather sofa and two upholstered chairs, arranged around a glass coffee table. A brick accent wall provides character, while a large television sits atop a wooden console. Artworks adorn the walls, accompanied by natural light from the windows.
Condo in Chicago
4.78 out of 5 average rating, 258 reviews

Logan Square Beauty with 2 Bedrooms W/parking

JamesRating, 5 stars2 weeks ago
Matt is a great host. Open, responsive and informative…everything you want really when on vacation
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 stars1 week 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.
Top guest favorite
A spacious living room features a comfortable couch with assorted pillows, a wooden coffee table, and an area rug. Large windows allow natural light to fill the room, accompanied by a ceiling fan and an entertainment unit. A decorative floor lamp and wall decor enhance the inviting space.
Condo in Chicago
4.92 out of 5 average rating, 348 reviews

Susie's Space. 2BR easy parking & pet friendly

RachelRating, 5 stars1 day ago
Susan’s home was comfortable, clean, well-equipped, and aesthetically pleasing. The bed I slept in was one of the most comfortable of my entire life—I prefer a soft mattress. As far as location goes, the street was quiet, good for walking our dog, and close enough to public transport. Plenty of buses were available. We used street parking for our car and never had problems with finding a close spot to the house whenever we did take the car out. We enjoyed the stay greatly and will stay again. Thank you, Susan!
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, 139 reviews

Modern Chicago Movie Themed Apt

LechelleRating, 5 stars2 weeks 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!
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 Chicago
4.98 out of 5 average rating, 165 reviews

Spacious 4 Bedroom Condo

ScottRating, 5 stars1 month 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.

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