
Vacation rentals in Pilsen, Chicago
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Top-rated vacation rentals in Pilsen, Chicago
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Popular amenities for Pilsen, Chicago vacation rentals
Other great vacation rentals in Pilsen, Chicago

Home in Pilsen
5 out of 5 average rating, 3 reviewsGorgeous home, 3BR/2BA, Free Parking, Free Laundry
재홍Rating, 5 stars2 weeks ago
Samantha was a wonderful host—she was very responsive and proactive in resolving any difficulties I faced, always with kindness. The space itself was spacious and well-suited for a family stay. I especially appreciated how well the bed was maintained, with a comfortable mattress and clean bedclothes. I would definitely choose this place again next time I travel to Chicago. My sincere thanks to the host!

Guest suite in Bridgeport
4.92 out of 5 average rating, 13 reviewsUrban Penthouse- Lux Rain Shower, Church View
VictoriaRating, 5 stars4 days ago
The hosts are the sweetest and most accommodating family. They have a lot on their plate, yet they were genuinely concerned about my needs. They allowed me to send my Amazon order to their place and even checked to make sure it had arrived. Despite some issues with the booking, they went above and beyond to ensure I was okay. I felt very safe during my stay. If I may offer some insights, it's important to note that the penthouse is located up 3-4 flights of stairs, as mentioned in other reviews. Additionally, be mindful of the parking situation in Chicago; you will need to go to the back to park. There is no sign indicating "Airbnb parking," so we had to use our best judgment, go through the wooden gate, and climb quite a few stairs (which can feel like a lot when you’re carrying things). The bathroom is a walkway that'll make sense later on. However, the hosts are willing to do anything to help!
Top guest favorite

Apartment in Bridgeport
5 out of 5 average rating, 12 reviewsBridgeport Garden Studio
KatRating, 5 stars3 days ago
This place was very cute, and the neighborhood feels like you can live there. There are a lot of unexpected items in the kitchen like nice gas stove, toaster oven. They did say that they don't have essentials but I found Shampoo and soap in the shower as well as in the bathroom sink. The space is very quiet, the Wifi is decently fast. Those stairs are a little tough to get down with your suitcase, but other than that, this was great. The owners is proactive about parking, giving you a pass on the days that there are events at the sox stadium to make sure that you don't get towed.

Apartment in Pilsen
4.73 out of 5 average rating, 169 reviewsLovely 2 bedroom apartment w/ Direct Porch Access!
JesusRating, 5 stars1 week ago
Victor is a fantastic host. He was courteous and was checking in on us and making sure our stay was going well. The apartment is great for a couple of people. Location is also good as it’s right next to a bus stop that takes you downtown and we felt that it was a quiet and peaceful neighborhood. Overall a great stay and a great value for staying in Chicago.
Guest favorite

Guest suite in Pilsen
4.93 out of 5 average rating, 28 reviewsPilsen Chicago's Art District Apartment
MicheleRating, 5 stars1 week ago
Very cute place, just what we needed for the weeken. my husband and I came down for the blues festival. which was absolutely amazing!! clean place, instructions were simple. Amelia was responsive in a timely manner. the set up, is exactly as shown in the pictures, the only thing about Chicago we didn't like is the parking, ughhh it is just like NYC, get in where you fit in, lol so, if you're lucky you can get a spot, in the front of the house or you can park around the corner, which is not far at all. so don't get discouraged. we will def go back just the two of us for another weekend. definitely get what you pay for. I do recommend this place. for a couple.
Guest favorite

Apartment in Pilsen
4.9 out of 5 average rating, 10 reviewsDuplex Luxury Apartment with King Suite
LinaRating, 5 stars2 weeks ago
Really beautiful place in a great location! Space was exactly as the pictures and had comfy beds/furniture! Cris was also very quick to respond and helpful. Would definitely stay here again.

Apartment in Chicago
4.52 out of 5 average rating, 110 reviewsHeart of Pilsen
MaximeRating, 5 stars5 days ago
Logement propre, calme et sympathique à quelques minutes du centre de Chicago. Transport en commun, metro de divers lignes, bus, trottinette en libre service à proximité. Station service avec snack à proximité de marche pour les achat alimentaires de dernière minutes. Literie confortable, j’ai adoré les oreillers

Apartment in Pilsen
5 out of 5 average rating, 4 reviewsStyle in Bridgeport
RoldanyRating, 5 stars1 week ago
Javier’s place was absolutely beautiful every detail was so thoughtfully styled, it truly felt like staying in a designer’s home. The space was comfortable, clean, and had everything we needed for a great stay. I instantly felt at home. The only slight challenge was parking at night, which could be a bit tricky. But honestly, the overall experience more than made up for it. I’d definitely stay here again!
Quick stats about vacation rentals in Pilsen, Chicago
Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ73 before taxes and fees
Total number of reviews
4K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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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
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club