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Holiday rentals with outdoor seating in West Side

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for West Side outdoor seating rentals

Holiday House Rentals with Outdoor Seating

Guest favourite
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
Guest favourite
Home in Chicago
4.96 out of 5 average rating, 173 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!
Top Guest favourite
Home in Wilmette
4.97 out of 5 average rating, 153 reviews

Unique porcelain-enamel paneled "Lustron" home

AnitaRating, 5 stars2 days ago
Great clean place
Guest favourite
Home in Chicago
4.93 out of 5 average rating, 43 reviews

Floresitas Oasis, your home in Chicago

KelvinRating, 5 stars1 week 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 favourite
Home in Chicago
4.95 out of 5 average rating, 63 reviews

Private Logan Square Garden Apt

Ana ClaudiaRating, 5 stars6 days ago
O espaço da Janice é extremamente aconchegante. A cozinha é super equipada (geladeira, fogao, cafeteira, panelas e demais utensílios... alem de manteiga e temperos básicos). O quarto é lindo e a cama super confortável. O banheiro estava limpo e havia itens de higiene de ótima qualidade, além de um excelente secador de cabelo. A televisão era grande e a sala super confortável. Amamos tudo. Quando voltar à Chicago, será a minha escolha!!
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 398 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

CarmenRating, 5 stars1 week ago
One of the best Airbnbs I have stayed at. It was beautifully decorated and super clean. Had everything I needed to feel comfortable and at home. The host was extremely responsive. The parking was a bit difficult but would not deter me from staying there again. Very close to downtown, about 10 minutes. Highly recommend.
Top Guest favourite
Home in Chicago
5 out of 5 average rating, 74 reviews

Windy City White House (3br/2ba) *New Listing*

SamanthaRating, 5 stars1 week ago
Beautiful place! Very clean! The host was very responsive. The kitchen was stocked with tea, coffee and extras. I love that they had a tea kettle. The rental had everything we needed, extra bedding and towels. We arrived to a basket of snacks and drinks 😊. Comfy beds and sofa in the sitting room. Lots of room for a family of 4. It is an upstairs unit so stairs to climb. Location was ok.
Guest favourite
Home in Chicago
4.94 out of 5 average rating, 35 reviews

Mid-Century Gem By United Center: Hot Tub & Sauna

MaraRating, 5 stars1 week ago
I had a fantastic stay at Sebastian’s place in Chicago! The house was spotless, stylish, and exactly as described. The location was perfect—close to restaurants, coffee shops, and public transportation, which made exploring the city super easy. Sebastian was a wonderful host: responsive, helpful, and made sure everything went smoothly. I especially appreciated the thoughtful touches throughout the home that made it feel cozy and welcoming. I would absolutely stay here again and highly recommend it to anyone visiting Chicago!

Apartment rentals with outdoor seating

Guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 197 reviews

iKlektik House Chicago / BlueJay

ARating, 5 stars2 weeks ago
We really enjoyed our stay here! Perfect for two people. This place is really cute and unique. Love the decor and seeing all the cool art projects. This place was within a couple miles of all the places we wanted to see, especially Soldier Field, so a Uber/taxi ride was cheap and very convenient. Super cute neighborhood too with beautiful row houses both modern and original. It is a nice quiet neighborhood as well and we felt very safe! We would recommend the Iklektik/Blue Jay house to anyone visiting Chicago that wants a comfortable and cozy experience!
Top Guest favourite
Apartment in Forest Park
4.98 out of 5 average rating, 233 reviews

Walk to Oak Park from this Newly Remodeled Gem

BeverlyRating, 5 stars2 weeks ago
Uncommonly well supplied and furnished, this is one of our favorite Airbnbs anywhere. We’ve stayed a few times, and our experience has always been exceptional.
Guest favourite
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!
Guest favourite
Apartment in Berwyn
4.92 out of 5 average rating, 382 reviews

Private apartment with retro vibe

DaltonRating, 5 stars2 days ago
Amazing stay with an amazing host! Antoinette runs a very nice place.
Top Guest favourite
Apartment in Oak Park
4.97 out of 5 average rating, 109 reviews

Cheerful Oak Park Apartment

StacyRating, 5 stars1 week ago
Spacious apartment with fun extras (puzzle, yoga mat, etc.)! It was easy-to-find and well-stocked with supplies, including thoughtful items for our use. It was clean and comfortable; we didn't use the kitchen at all as it was a very quick stay. The hosts are cognizant of the noise from the train and highway, and provide earplugs, sound machines, blackout shades, a fan, etc., to help ensure guests can sleep well. The local recommendations were great. Downtown Oak Park is about a 10-minute drive; we appreciated the ability to walk 5 minutes to a nice café or restaurant.
Top Guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 118 reviews

Belmont Pleasures - hot tub / arcade gaming room

AustinRating, 5 stars2 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.
Superhost
Apartment in Chicago
4.87 out of 5 average rating, 105 reviews

McCormick 2B/2Ba corner unit/opt parking/sleeps 6

CopeyRating, 5 stars4 weeks ago
I came for the Beyoncé concert and the place was pristine. It was kind of a perfect storm of things.
Top Guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 105 reviews

Cozy Studio in Perfect Location

AmoryRating, 5 stars1 week ago
This is a really nice spot. Had everything we needed. Lot of small shops and restaurants nearby. If you like to walk (which we do), downtown Chicago is only a couple miles away. It’s also not too expensive to uber there either. Had a great time!

Condo rentals with outdoor seating

Guest favourite
Condo in Chicago
4.95 out of 5 average rating, 178 reviews

3 BR GetAway, 15mins to Loop + private parking

EglantineRating, 5 stars1 week ago
Super séjour nous étions 5, bien aménager,équipement parfait, très propre, hôte très accueillant et réactif, à 10min à pied de la Green ligne, quartier très calme supérette à 15min à pied.
Superhost
Condo in Chicago
4.78 out of 5 average rating, 257 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 favourite
Condo in Chicago
4.91 out of 5 average rating, 110 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

NicolasRating, 5 stars6 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.
Guest favourite
Condo in Chicago
4.93 out of 5 average rating, 139 reviews

Modern Chicago Movie Themed Apt

LechelleRating, 5 stars1 week 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 favourite
Condo in Chicago
4.98 out of 5 average rating, 165 reviews

Spacious 4 Bedroom Condo

ScottRating, 5 stars4 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 favourite
Condo in Chicago
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 favourite
Condo in Chicago
4.83 out of 5 average rating, 314 reviews

Welcoming 2BR in Chicago's Best Neighborhood!

PhilRating, 5 stars2 weeks ago
Great stay at Kathleen's! We already knew we loved the area having lived a few blocks away for many years so we felt right at home. Perfect for guests with an infant or toddler - nice high chair and pack-n-play, our little one slept and ate well all week.
Guest favourite
Condo in Chicago
4.91 out of 5 average rating, 165 reviews

East Garfield Park 2 Bedroom

StefanRating, 5 stars2 days ago
Great place to stay close to train line. Helpful friendly host He even supplied snacks and water which was very thoughtful. Nice place as described.

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