
Holiday rentals with outdoor seating in West Side
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in West Side
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Holiday House Rentals with Outdoor Seating

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

Chicago River House -BBQ Oasis now open!
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!

Unique porcelain-enamel paneled "Lustron" home
Great clean place

Floresitas Oasis, your home in Chicago
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!

Private Logan Square Garden Apt
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!!

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

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

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

iKlektik House Chicago / BlueJay
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!

Walk to Oak Park from this Newly Remodeled Gem
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.

Logan Square 2nd Floor Chicago Victorian
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!

Private apartment with retro vibe
Amazing stay with an amazing host! Antoinette runs a very nice place.

Cheerful Oak Park Apartment
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.

Belmont Pleasures - hot tub / arcade gaming room
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.

McCormick 2B/2Ba corner unit/opt parking/sleeps 6
I came for the Beyoncé concert and the place was pristine. It was kind of a perfect storm of things.

Cozy Studio in Perfect Location
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

3 BR GetAway, 15mins to Loop + private parking
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.

Logan Square Beauty with 2 Bedrooms W/parking
Matt is a great host. Open, responsive and informative…everything you want really when on vacation

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
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.

Modern Chicago Movie Themed Apt
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!

Spacious 4 Bedroom Condo
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.

Wicker Park/Bucktown condo with large balcony
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!

Welcoming 2BR in Chicago's Best Neighborhood!
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.

East Garfield Park 2 Bedroom
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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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
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