
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

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

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.

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
Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!

Celebrate at Hacjenda house
I had such a great time at the Hacjenda House! I came here with my dog for a peaceful getaway and it was exactly that. Lena set up the fireplace inside for me and I was cozy all night. Plenty of firewood in their backyard. Super spacious and beautiful inside and out. Their tub upstairs is also so spacious for a bath. Lena was so kind by checking in on me throughout my stay. I didn’t want to leave. I definitely want to come back.

Luxury Loft with Private Pool and Movie Theater
Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

Luxury fenced in modern ranch
It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!

LUXURY - Movie Theater + Spa House
Nicholas was great house was really nice will definitely be back
Weekly house rentals

The Modern Muse of Chicago! Close to everything!
Jasna was an amazing host! The house was absolutely spectacular—truly even better than the photos. Every room felt thoughtfully designed and full of warmth, making it feel just like home. We had all the amenities we needed, which made our stay super comfortable and stress-free. It was the perfect setting for a special girls’ trip with my mom and sister. The neighborhood was peaceful and beautiful, adding to the relaxing vibe. We’ll definitely be back! Thank you again for everything, Jasna!

Stylish Haven Near Loop in Sought After Pilsen
The house was exactly what it shows in pictures. Everything was clean and impeccable. The neighborhood was also really safe and quiet. I would definitely be back!

3bd/3ba Bronzeville Beauty
The hosts’ of this property were great and accommodating. They catered to our altered schedule and compromised on a request of ours. We will definitely stay here again.

Animal House near Sox stadium
If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.

Floresitas Oasis, your home in Chicago
Lizbeth was an amazing host. She’s responsive and attentive. The place was exceptional clean and had an amazing smell. I was there to celebrate my birthday and was pleasantly surprised upon entry when I was greeted with a personalized birthday message, fresh flowers and a bottle of wine. Anytime I reached out to Lizbeth, she responded expeditiously. Again, very attentive. My husband and I will definitely stay at her beautiful Oasis again. We felt comfortable and completely safe. Everything we wanted to do was a quick drive from the location. If you’re considering staying at her home, you will not regret it. If I could give more than 5 stars, I would. Thanks Lizbeth for being an incredible host Until the next time…

Sunny Historic Cottage on the Park
We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.

Ideal Group Getaway: Best Location, Parking, Patio
Great place. Great location. No issues at all. I would rent again. It's a good spot between the Gold Coast and Lincoln park and beer some really good restaurants. Place was as described and would have no issues staying there again.

Vintage Urban Retreat | Oak Park
Definitely recommend staying here! Our group came in for a wedding and the house had everything we needed to get ready and feel comfortable doing so. I can’t tell you how relieving it is to walk into a BNB and literally know it will accommodate your needs. Very clean, fully accommodating kitchen with pans and scissors and coffee and supplies. The air conditioning kept us cool on one of the hottest weekends in Chicagoland. Easy to get in and out of especially for multiple people coming and going at different times. The beds were comfortable and the linens were pristine. We rented a couple other houses in the area and we all agreed this one was the best. Also, Gabriela was incredibly helpful, easily accessible, and overall a great host. Highly recommend! We will be back!
Private house rentals

Bronzeville Home! Downtown + McCormick + U of C
Great place for my family to stay! Rides to downtown, Navy Pier and Hyde Park were short and the kitchen and living room were very spacious. Henok was very kind and flexible!

Amazing historic campus mansion!
Caryl was extremely helpful with a check in process and she introduced us the property as well as surrounding local attractions. We felt the place was warm and very spacious for our group and we had a pleasant stay.

CasaNova Modern City Living
Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath
We had a truly wonderful stay at Casa22. The home is beautiful, luxurious, and impeccably maintained — everything was clean, spotless and thoughtfully arranged. It had all the essentials we needed for a comfortable extended stay with our family, including a well-equipped kitchen, and spacious layout. The hosts, Narcis and Gabriel, were fantastic — extremely responsive, clear in their communication. They provided detailed instructions that made check-in, check-out, and everything in between seamless. The neighborhood is quiet, safe, and very family-friendly, with easy access to main roads — a great location if you're planning to explore Chicago without the stress of city parking. Having a car made it easy to get around, and the area itself felt peaceful and well-kept. If you're visiting the Chicago area and looking for a clean, elegant, and well-managed place to stay, I highly recommend Casa22. We would absolutely love to return!

jane's house - a boutique flat in west town -2b/1b
We absolutely loved staying at Amy’s place! Easy check in/check out, great communication by the host, and plenty of room for 2 adults and 2 kids to stretch out. The mid century vibe was a nice bonus. Would 10/10 stay here again.

Oak Park - Wine House!
I would like to share that all the descriptions, location and accommodations were exactly as described. This home is both comfortable and stylish. It is important to mention that the house was very clean. On a different note, all the details have been looked at, TV, games, furniture. The house is very close to the train, coffee shop and a breakfast place.

Executive Contemporary Duplex
Perfect location! Not far from the best things to do in the city. The neighborhood is quiet and safe. I would highly recommend!

Grand Retreat/5Brs/Game Room
Very nice, comfortable house with room for family to spread out. Very clean w good amenities (plus a few welcoming chocolates)! Grandkids enjoyed the PAC Man game in the game room as well as shooting baskets!
Quick stats about house rentals in Pilsen, Chicago
Total rentals
30 properties
Nightly prices starting at
₹1,720 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
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Six Flags Great America
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Brookfield Zoo
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Moraine Hills State Park