
Apartment vacation rentals in Pilsen, Chicago
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Top-rated apartment rentals in Pilsen, Chicago
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pilsen, Chicago apartment rentals
Weekly apartment rentals

Style, comfort, and convenience
Apartment is as expected based on pictures. Very clean space and peaceful part of town. Easy check in/check out instructions. Would book again!

Al Capone Era Speakeasy 3 BR
For basics, it is very clean and comfortable with a well appointed kitchen, comfortable beds, and easy street parking. The space itself is remarkable. Patterned tin walls and ceilings, a triangular shape, nicely decorated, and the construction details from converting it to an apartment are all in keeping with the style. We loved it.

Cozy Chicago Apartment next to the River
Very walkable to public transit, super comfortable sleeping arrangements, and beautiful apartment in general!

Heart of Pilsen
Thank you for a wonderful stay! You were very accommodating.

Cozy Pilsen Apartment
It was exactly what we needed for a weekend getaway. A great place to come back to each evening after a day of adventure. Easy walk to the Pink 'L' train that will take you right into downtown for a few bucks. Coffee shops and restaurants all within walking distance. We can't wait to come back to do the things we couldn't fit in. Thanks Rosa for sharing your home.

Prime Bridgeport - McGuane Park
This 2 bedroom, 1 bath garden apartment was perfect for 2 people. It was within walking distance to Chinatown and Sox Park. Very quiet. Its next to a lovely park.

Loft-Inspired Retreat | Stylish Stay Near Downtown
Loved being just a couple blocks from the Western Pink Line station and bus stops both north-south and east-west.

NEW Jade Haven in Berwyn/Riverside
Well kept, quiet environment. Host is responsive.
Private apartment rentals

Cool spot in cool neighborhood
Next to the trains, a apartment with separate bedroom, living room, kitchen and bathroom, even a laundry room available if necessary and a host who responds quickly and does not hesitate to give advice on Chicago. I highly recommend!

Mins. to Downtown & West loop! Entire Apt.
Great location, lots of good restaurants in Pilsen neighborhood and still quite close to downtown.

Modern Studio Apt Free Parking Wi-Fi Self Check-In
Cam’s place was a great find — spacious, clean, and surprisingly quiet despite being on a busy street. The photos don’t do justice to how much room there is. The layout is unconventional but adds character, and everything is well thought out. The kitchen is fully stocked, there are plenty of towels, and the TV area is perfect for relaxing, comes with private parking. Located in a safe neighborhood just minutes from the Orange Line, it’s super convenient for getting around Chicago. I already miss this place — absolutely worth every penny.

Large private lower level suite
Missy was a great host, very quick to respond and offers resolutions quickly. this is the second time my family has stayed with Missy and she's a great host

Designer Avondale Attic
Einfach nur wundervoll. Das war eine der schönsten Unterkünfte, in der ich je war. Die Wohnung ist total liebevoll eingerichtet. Alles war super sauber und ordentlich. Es gibt sogar Zahnbürsten, Zahnpasta und eine Schlafmaske, falls man sie benötigt. Die Küche ist auch super ausgestattet mit allem was man braucht. Der kurze Weg zur Metro war ebenfalls sehr praktisch. Wir würden definitiv wieder kommen.

Lincoln Paradise– Steps to Park & Zoo!
Our second stay here-- all is wonderful!! Well appointed space, fabulous bed and pillows. Everything you need is in the kitchen. The location cannot be beat -- across the street from the park. Would absolutely come again!!

Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
Working with Laura was a pleasure from start to end. Our trip went smoothly and we appreciated the living space for the 3 people in our party. We got lucky with parking each day, it was so close to our unit, also with the nearby market and restaurants. It was a perfect distance from Chicago for us. We drove into the city to enjoy the sights and sounds of Chicago then happy to drive back into a quieter neighborhood. We would definitely recommend this unit. Thank you Laura for letting us stay at your cozy home!

Explore Lincoln Park from a Polished Apartment
There is no way I/we can do a review of Elizabeth's beautiful apartment in just 1,000 characters. Met Elizabeth personally, made a wonderful connection. It's the most awesome airbnb we've ever stayed at. The apartment has been beautifully remodeled. As a retired general contractor, I was very impressed. The neighborhood is fantastic; great for walking, shopping, and there are restaurants galore. The location is fantastic for touring Chicago. The neighborhood is beautiful with lovely architecture and interesting shops. There are lots of families; couples walking, biking, babies-buggying. We enjoyed walking around the neighborhood after a walk to dinner or lunch. The bed/bedding is very comfortable and we slept very well. Great temp control, lots of windows, and a 65"flat screen TV. The bathroom is large and airy with a walk-in shower. The unit is very quiet, with dual-pane windows and black-out shades for sleeping in late. Stay here for the best Chicago experience.
Apartment rentals with a hot tub

Skyline Oasis: City & Lake Views
Perfect weeklong stay in Chicago! The apartment is well equipped and makes you feel right at home. The building is connected via sky bridge to Jewel making it easy to grab groceries. The location cannot be beat - easy access to West Loop, Wicker Park, River North. The hosts were fantastic and flexible with our check in times. Looking forward to coming back!

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.

Rooftop HotTub As Seen On "Married At First Sight"
I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!

Large Studio Apartment with no cleaning fee
David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.

Penthouse Near Fulton: Skyline, Spacious
Great place nice views , communication with host very smooth !

Sentral 1 Bedroom Apt in South Loop Chicago
Sentral worked great for us going to a graduation for a long weekend. Unit is exactly as described, modern, and clean. Kitchen utensils are reasonable while shelves and refrig are empty save for some coffee so if going to cook/eat be sure to bring everything such as butter, spices, etc. - a Trader Joes is 3 blocks away. Price is not cheap but is very convenient and easy so on balance okay for us. Front desk is very helpful and cheerful.

Belmont Pleasures - hot tub / arcade gaming room
Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.

2Bed 2Bath 15min to Wrigley with Parking& Balcony
Clean and cozy home with a friendly host!
Quick stats about apartment rentals in Pilsen, Chicago
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
2.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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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