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

Stunning Home in Prime Chicago with Private Pool
We fully enjoyed our stay! The home is exactly as described — clean, spacious, and in an amazing location close to great restaurants. It was so nice having a full house with an amazing pool to relax in. Communication with the host was excellent, and everything went smoothly. A perfect and affordable option — we would definitely recommend and plan to return in the future!

Luxury Loft with Private Pool and Movie Theater
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!

LUXURY - Movie Theater + Spa House
Weekly house rentals

Duplex Home RoscoeVillage/Wrigley Free St Parking
2nd time staying at Sharleen’s place—wonderful experience! We like location, friendly and quiet neighborhood, walkable to restaurants. We would recommend to guests looking for a space in Roscoe. 🙂

Spacious Five Bedroom Home in Trendy Chicago Neighborhood
The house was gorgeous and so comfortable for our large family gathering. It was very well equipped. The kids had a blast, the adults were able to relax. Different areas to hang out. Great kitchen space.

Warm and comfortable inviting Suburban home !
Nice spot - place was very clean, comfy beds, lots of seating areas that were also comfy. We got used the the sounds of the trains after the first night. Bumped into Rich one day while he was mowing the grass; he was very kind. The place is a little older, but that’s in the description. We couldn’t figure out how to get the stove to turn on so we heated food in the microwave and on the gas grill outside. Neighborhood was very quiet and peaceful, and we liked having the fenced yard for our dog.

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
Thank you for allowing us to enjoy your home. It was a wonderful experience. It is incredible. The place is very cozy. You feel an atmosphere of relaxation and peace.

Wrigleyville Greystone
We had a great stay at Mark's place in Wrigleyville. Extended family gathered to celebrate a college graduation, and the location was excellent. Beautiful house in a safe neighborhood with easy walk-to access to the L and tons of nearby places for coffee, food, drink. Mark was an awesome host. Check in was smooth with great communication throughout our stay. Definitely on our return visit list.

Excellent Location for Vacation or Business Stays.
Everything was exactly as described. Great communication. I would definitely rent this property again.

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN
Nice place, quiet and comfortable and we loved the neighborhood
Private house rentals

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
Happy that this place was available! It was comfortable, clean, and roomy, right in Pilsen. Excellent communication and overall great spot.

Gorgeous and Luxurious 3 BR Home
rob and sue were great hosts. easy, timely communication. the house has everything you’ll need and is spacious and quiet, despite being close to some busy streets. walkable to diners, restaurants, and some shopping. . will definitely book again.

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 stayed here for my Bachelor Party. It was a golf trip, so having the Preserve at Oak Meadows right next door was great. Jazmin was responsive when we had a small issue with the code to get in. All-in-all a great place!

Quiet cul-de-sac with huge fenced in backyard
The place was lovely—clean, comfortable, and just as described. Tom was very communicative and easy to reach, which made everything smooth and stress-free. One thing to note: there were several air fresheners throughout the house, which created a strong scent. We're a bit more sensitive to smells, so it was something we definitely noticed and found a bit challenging. If you're sensitive to artificial fragrances, it's just something to keep in mind before booking. Otherwise, it was a great stay!

A serene haven perfect for the whole family!
Her place is very nice. It’s so cozy and cute. She supplies everything you need even though I came with what I needed. She is very accommodating. I love a cozy at home feeling. Very clean as well. Thank you I definitely will be booking again.
Quick stats about house rentals in Pilsen, Chicago
Total rentals
30 properties
Nightly prices starting at
£15 before taxes and fees
Total number of reviews
810 reviews
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Flossmoor Golf Club
- Willis Tower
- Museum of Science and Industry
- Wicker Park
- Lincoln Park
- Chicago History Museum
- Skokie Country Club
- Illinois Beach State Park
- Washington Park Zoo
- Brookfield Zoo
- Chicago Cultural Center