
House holiday rentals in West Side
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Top-rated house rentals in West Side
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Popular amenities for West Side house rentals
House rentals with a pool

Pardizes Suites
I was speechless when I walked in her house it was beyond beautiful nothing was out of place at all when I say she had everything you can think of to accommodate us all she had all the toiletries you could think of the kitchen was stocked with all kind of seasonings dishes she even stocked breakfast sausages she put balloons out she really out done herself she went above and beyond it was plenty of games there the rooms were beautiful the beds were so comfortable I didn’t want to get up it was the best airbnb I ever stayed in we were all blown away by how beautiful and clean and neat it was Lisa is a very great hostess you all make sure to book with her she is great

Munster hide away
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area 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!

Stunning Home in Prime Chicago with Private Pool
Excellent place with lots to do. Local restaurants had delicious food, place was very clean and inviting. Will definitely be booking again in the future

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

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.

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!

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.

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 .

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.

Modern Victorian Charm | A+ Location in OP
Great place to stay while visiting family! Very kid friendly and baby items provided too! Loved this home away from home!

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.

Mid-Century Gem By United Center: Hot Tub & Sauna
Great stay! Loved the decor and amenities. Everything was just as described and my family really enjoyed our time there. Would stay again!
Private house rentals

Chicago Home (1st floor) by Midway near Downtown
This was the perfect location just out of the city but a 15 minutes drive to solider field. The rooms were awesome for our group and we really enjoyed our time, would definitely stay again next time I am in Chicago

Stylish Haven Near Loop in Sought After Pilsen
Kyriako, thank you for everything. We had a great stay!

The Modern Muse of Chicago! Close to everything!
This Airbnb exceeded our expectations in every way! It was even better in person—much more spacious than we anticipated. The home was stocked with thoughtful amenities, especially in the kitchen, which made our stay incredibly convenient. The outdoor seating area was a great place to relax, and we loved the location. It truly felt like a home away from home, with everything we could possibly need already there. The host was also very attentive and accommodating, making the experience even better. We would definitely stay here again!

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.

Spacious Designer Oasis: Game Room - Yard - Garage
I had an amazing stay at the Spacious Designer’s Oasis, Oak Park, IL! The house was centrally located, making it easy to get around and explore the area. It was impeccably clean, beautifully designed, and had the perfect balance of open space and cozy, modern charm. Every room felt thoughtfully curated and comfortable. A special shoutout to Rameez, our host—he was incredibly responsive, warm, and welcoming from the very start. He made sure we had everything we needed and went above and beyond to ensure our stay was seamless. I’d absolutely stay here again and highly recommend it to anyone looking for a stylish and relaxing place to stay. Thanks again, Rameez!

Big house in the BEST Location!
We had a wonderful stay. The house was clean, we had all we needed to make meals and the beds were comfortable. We would have appreciated blinds in the two smaller bedrooms but enjoyed the rooms nonetheless. My friends say Thank you for your hosting.

Charming Oak Park 4bd/3.5ba and 2 Private Parking
David’s place was AWESOME!! Everything was great and homie. David was awesome with responding and made sure we were good. I had two past reviews in which they could have easily sparked David to not let me book with him. But he was open minded and heard me out unlike some other host. All reviews are not honest and the details can be off by mishaps. But I appreciate his openness, niceness and overall just awesomeness. Definitely an awesome place for an affordable price. The neighborhood is nice as well and a great out door seating area in the back yard. I’ll be booking again. THANK YOU DAVID ❤️

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 !!!
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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
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Wicker Park
- Willis Tower
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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