
House holiday rentals in West Side
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Top-rated house rentals in West Side
Guests agree: these houses are highly rated for location, cleanliness and more.
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Popular amenities for house rentals in West Side
House rentals with a pool

Pardizes Suites
It was a gorgeous home, she knew we were coming for my husbands bday and she got us a bottle of wine and balloons. She was very helpful and responsive if we needed anything. Great place to stay!

Glen Ellyn Home
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.

Spacious 3 Floor Townhome
Super cool host, very flexible and kind. When I come back im definitely going thru him again!

Rosemont 4BD2BA house with Pool
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

Now Open: Heated Pool with Entire House
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.

Schaumburg Oasis:Private Pool & Enchanted Garden
We stayed here while our floors were being refinished and Marzena’s Oasis did not disappoint! You can tell she takes great pride in her listing; everything was as described and more. The home was very clean with plenty of linens, dishes, and kitchen/pantry supplies. My kids left more crumbs on the floor than usual during breakfast one day…I could not find a broom so I messaged Marzena. She dropped off a stick vacuum AND some delicious treats. Above and beyond to make us feel welcome and comfortable. Thank you for a home away from home!

Spacious 4 Bed/3.5 Bath Sleeps 8+
Beautiful house very clean and comfortable. We'll be back very soon

Paradise 4BR w/ Pool & Games
We recently moved backed to the Chicagoland area from Texas. We needed a place to stay while our Chicago home was being renovated. Lily’s place was perfect. It had everything we needed for the duration of our extended stay. It was well appointed. Exceptionally clean. It had all the amenities necessary for our family to live comfortably and it was close to grocery stores, shopping, restaurants, and downtown Chicago. Highly recommend.
Weekly house rentals

City Cottage in Logan Square-Avondale
We loved this cute little house! Super walkable and close to lots of stuff in Logan Square; although we thoroughly enjoyed the peacefulness of hanging out in the private backyard. Would definitely stay again!

Rooftop Access with Views and Gym - LCP Collection
Great location, clean, spacious, great linens and towels.

NEW! 3BR/2.5B Duplex in Noble Sq
Host is very accommodating and responsive. The place is nice and was in a great location. Only a short 10 minute drive that was a straight shot to Michigan Ave. The only thing we felt was slightly misleading was that we were under the impression that the 3rd bedroom with a couch was able to pull out and convert into a bed. Unfortunately, that wasn’t the case, so we ended up leveraging an air mattress we had packed as a contingency. Overall, we had an enjoyable stay and would recommend.

Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Great stay and easily accommodated ng larger in laws family

Exquisite Chicago Modern Rooftop, Sleeps 9
I love everything about this home and all the e amenities, and the private rooftop was the greatest touch of the property Vince was amazing and very easy to reach in very fast responding.Thanks so much .

Spacious whole apt near shopping and city
This was my first time using Airbnb and Daniel was so helpful through the entire process. Also the house was so clean and smelled so good! Pictures looked just like online. Parking was easy and didn’t have trouble or finding anything at all.

Modern Victorian Charm | A+ Location in OP
This was a fantastic find in the Oak Park area! Within walking distance of a lot of great restaurants and public transit that leads directly into the city. Anything that wasn't walkable was just a short drive. Gabriela was super helpful and flexible where possible, and the house itself was well stocked with basics. If I'm ever back in the area, I'd absolutely consider staying with them again.

① Lux | Spa | Rooftop | Modern | 4 Mi to Downtown
Anita’s place was absolutely stunning and looked just like the photos. Extremely clean and very spacious. We hosted a 50th birthday brunch here and it was more than enough space and amenities to accommodate everyone. The rooftop was just amazing and a great addition to the place. Thank you Anita for letting us book your gorgeous home and we would love to book again and again! ⭐️⭐️⭐️⭐️⭐️
Private house rentals

European Custom Built Home
House is vast, clean, and absolutely beautiful inside and out. Easy to get with a car or local transit and a short walk. Pictures don't do the house justice it has lovely historical features and more room than it seems between the three floors (ground floor, basement and upstairs). With two usable balconies and a patio backyard there is more enough space to entertain a small group outside.

Perfect Location Across from Park & Train Station
The house was beautiful and was perfect for our group. Everything was spotlessly clean and just as described. Access to the El was convenient but also created quite a lot of noise especially in the front of the house. This, of course, is completely out of the host’s control and we got used to it after 24 hours or so. The location was also convenient to the interstate that flows right into downtown, which was great for us as we were participating in a conference in a hotel on Michigan Avenue. Overall we had a great experience with the house and the host. Would recommend this location very highly.

Big house in the BEST Location!
It was as pictured and suited our needs. Clean and well organized. When we reached out we were responded to promptly and thoroughly. The location is good and walkable. If planning to go to Navy Pier or the Miracle Mile to go shopping (or something in that general area of Chicago), expect about a 40 - 60 min drive.

jane's house - a boutique flat in west town -2b/1b
Jane's house was the ideal accommodation for our visit to Chicago. The apartment was very well equipped. The area is very pleasant and it is also easy to get into the city or to the airport by metro and bus. Thanks again to Amy and Dean.

Oak Park - Wine House!
We had a wonderful stay at Oak Park Wine House !!! There was so much room for all of our family to have their own space and also come together for meals and games. The fresh flowers were beautiful touch to the dining area. The location was perfect ! A nice place to walk our dog, grab yummy pastries and coffee and enjoy the surrounding art. Also was close to downtown for us for our planned day trips!!! Would highly recommend and book here again !!!

Fully Renovated! only 15 min away from Downtown!
Very clean apartment and host was great. Everything was just as described and I would recommend it to a friend.

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
It was a really nice stay. We rented it out for my sister's bachelorette party, and it comfortably accommodated all of us. Adam responded quickly to any questions that I had.

West Town Oasis: Hot Tub + Garage
great stay. location was wonderful
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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
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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