
House holiday rentals in West Loop, Chicago
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Top-rated house rentals in West Loop, Chicago
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Popular amenities for house rentals in West Loop, Chicago
House rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.

Cozy house in Schererville
Kate’s place was exactly what I expected. Pristine condition and spotless. Kate accommodated my early arrival which was greatly appreciated. I would 100% book this place again. Highly recommend her place to anyone in the area for a weekend or just to get away from the city. Thank you again for your attention on such a short notice on my booking.

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.

Great Kayaking, biking, hiking get away
Check in was easy, and everything was as described. Julie’s place met our needs for a place to stay while visiting family. Her place is clean and well supplied. Lots of room which we didn’t use all of it. The fenced in area was nice to be able to let our dogs out.

Whole House With Hot Tub And Spacious Bedrooms
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again

Entire House With Pool - Backyard Beach Getaway
This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10

Beautiful Spanish style Home (w/inground pool)
House was lovely. I enjoyed the homes decor. Every day I woke up with something else I loved. The house had everything we needed. Only thing I wished the pool heater was working and the pillows were flat. I would definitely stay here again.

Bayless Dune Lodge at West Beach - Indiana Dunes!
We had a great weekend getaway from Chicago and it was less than an hour (without traffic) away! Peaceful, quiet, near the beach. Cullen was an awesome host!
Weekly house rentals

Tropical Penthouse in Wicker Park w/Backyard Patio
Great Airbnb for a bachelorette party! Tons of space, beds and a great location in Chicago even for a local group. The hosts were very easy to communicate with. I would recommend the space to anyone looking for an Airbnb for a large group!

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Matt was a wonderful host and very responsive. The house was exactly as described. It felt like a home away from home. Everything you need is provided for you. I was traveling with my teen sons and we enjoyed the hot tub each night and watched a movie while soaking and relaxing. The house is on the Southside of the city and which was a nice break from the buzz of downtown. The train is about a 20-25 minute walk and the White Sox stadium is right near there. I definitely recommend this place if you’re looking for a home in Chicago.

Duplex Home RoscoeVillage/Wrigley Free St Parking
We enjoyed preparing pizzas from scratch in the perfectly sized kitchen with our adult kids who live in Chicago and their friends. There was plenty of space to sit around the spacious kitchen island and talk while cooking. The whole experience was made even better by using the Wolf stove top and Bosch wall-mount oven, which produced perfectly crisp crust and tasty toppings. The neighborhood felt safe and peaceful while providing everything we needed within walking distance. Parking was also easy. We had no trouble finding a space in front of the house all 4 days we were there. As a special bonus, a new chocolate cafe opened a few days ago (Hotel Chocolat Velvetiser Cafe) and is just a short walk away! We had a great time in this lovely home.

Spacious Five Bedroom Home in Trendy Chicago Neighborhood
Great experience at Casey’s place. The home is as well stocked with kitchen essentials and extras as any place that we have ever stayed. There were toys for the kids and the design of the place was awesome. We had a great stay and would definitely come back.

The Avondale Guesthouse
We absolutely loved the place! Great location, price and space! Jed was so kind and responsive, and we absolutely loved the the outdoor space! We would definitely stay again!

The Spa of Downtown Whiting
a really awesome place. I highly recommend this place.

Excellent Location for Vacation or Business Stays.
This was our second stay at Rita’s and we found it very accommodating and great of an experience as our last visit. The neighborhood is in a great location and it is cozy and quiet. The property was extremely clean. We would be happy with staying here again in the future.

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN
Felt safe in the area . Easy parking . Close to CTA train and one stop away from our destination. Clean and quiet home felt like home also . I highly recommend this place if you attending any event at the united center and want to visit cloud gate easy directions. Joyce thanks for the wonderful stay .
Private house rentals

Spacious Full Home Near the Heart of Wrigleyville
We had an amazing stay at Dustin’s place! We had a group of 9 ladies who fit perfectly with plenty of cozy beds and linens. The location was very walkable and we felt safe. We walked over to Barcocina Lakeview on Friday, and then jumped on the train to River North on Saturday to celebrate St. Patrick’s Day. We had a couple of questions during our visit, and Dustin was speedy on the replies! Everyone in the group said the experience was 10 out of 10. We hope to visit again.

Des Plaines Home
I travel a lot for work, and this was by far one of the best places I've ever stayed! Kris was so kind and responsive. We were all in love with the house, and my partner repeatedly said they wanted a house just like it! We were close to a cute downtown with great coffee and only 15 minutes from the Allstate arena. The couches were so comfy and the kitchen was well stocked with appliances and even containers to put leftovers in. If we are ever in the area again I hope we are able to book this bnb again.

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.

Casa PLZN Location | Entire Home | Garage Parking
Great place near restaurants and cafes. Garage access is a plus. Train noise is noticeable at first but you get used to it and it's only noise as the house doesn't rumble when the train passes.

Gorgeous and Luxurious 3 BR Home
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.

Grand Victorian Mansion in Austin Area
The accommodation was spacious and very comfortable for our large group of 16. While the floors creak a bit, it wasn’t an issue. Samantha was always quick to address any questions and issues. The gated parking area provided ample space for our cars, which was a great convenience.

Home in the Woods!
We had such a wonderful time at Jazmin Airbnb. The place was clean and smell great! She was very responsive and we had no issue with checking into our Airbnb. Thank you for being such a great host!

Quiet cul-de-sac with huge fenced in backyard
Absolutely loved staying here. Tom was an awesome host. He has very detailed instructions throughout the house for everything from connecting to the WiFi to how the individual tvs work. The couch in the living room is stupid comfortable and the master bedroom was cool and dark. 10/10 would stay here again
Quick stats about house rentals in West Loop, Chicago
Total rentals
20 properties
Nightly prices starting at
£53 before taxes and fees
Total number of reviews
1K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- The Field Museum
- Lincoln Park Zoo
- Six Flags Great America
- Promontory Point
- Museum of Science and Industry
- Brookfield Zoo
- Humboldt Park
- Skokie Country Club
- Illinois Beach State Park
- 875 North Michigan Avenue
- Skydeck Chicago
- Splash Station
- Flossmoor Golf Club
- Villa Olivia
- Raging Waves Waterpark
- Moraine Hills State Park
- Lincoln Park