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Apartment vacation rentals in Pilsen, Chicago

Find and book unique apartments on Airbnb

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Popular amenities for Pilsen, Chicago apartment rentals

Weekly apartment rentals

Top guest favorite
Apartment in Little Italy
5 out of 5 average rating, 45 reviews

Style, comfort, and convenience

AshleyRating, 5 stars1 week ago
Apartment is as expected based on pictures. Very clean space and peaceful part of town. Easy check in/check out instructions. Would book again!
Top guest favorite
Apartment in Bridgeport
5 out of 5 average rating, 23 reviews

Al Capone Era Speakeasy 3 BR

TimRating, 5 stars1 month ago
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.
Top guest favorite
Apartment in Bridgeport
4.98 out of 5 average rating, 52 reviews

Cozy Chicago Apartment next to the River

MadelineRating, 5 stars1 week ago
Very walkable to public transit, super comfortable sleeping arrangements, and beautiful apartment in general!
Superhost
Apartment in Pilsen Historic District
4.69 out of 5 average rating, 188 reviews

Heart of Pilsen

FaithRating, 5 stars1 month ago
Thank you for a wonderful stay! You were very accommodating.
Superhost
Apartment in Chicago
4.83 out of 5 average rating, 54 reviews

Cozy Pilsen Apartment

ToryRating, 5 stars1 week ago
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.
Guest favorite
Apartment in Bridgeport
4.91 out of 5 average rating, 78 reviews

Prime Bridgeport - McGuane Park

PatriciaRating, 5 stars2 weeks ago
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.
Guest favorite
Apartment in Chicago
4.9 out of 5 average rating, 21 reviews

Loft-Inspired Retreat | Stylish Stay Near Downtown

EvanRating, 5 stars1 week ago
Loved being just a couple blocks from the Western Pink Line station and bus stops both north-south and east-west.
Superhost
Apartment in Berwyn
5 out of 5 average rating, 4 reviews

NEW Jade Haven in Berwyn/Riverside

ZakiraRating, 5 stars3 weeks ago
Well kept, quiet environment. Host is responsive.

Private apartment rentals

Superhost
Apartment in Chicago
4.73 out of 5 average rating, 11 reviews

Cool spot in cool neighborhood

JulietteRating, 5 stars1 month ago
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!
Guest favorite
Apartment in Pilsen Historic District
4.92 out of 5 average rating, 105 reviews

Mins. to Downtown & West loop! Entire Apt.

InesRating, 5 stars2 weeks ago
Great location, lots of good restaurants in Pilsen neighborhood and still quite close to downtown.
Superhost
Apartment in Bridgeport
4.9 out of 5 average rating, 86 reviews

Modern Studio Apt Free Parking Wi-Fi Self Check-In

UrizRating, 5 stars1 week ago
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.
Guest favorite
Apartment in Bridgeport
4.95 out of 5 average rating, 19 reviews

Large private lower level suite

LucasRating, 5 stars1 week ago
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
Guest favorite
Apartment in Avondale
4.97 out of 5 average rating, 162 reviews

Designer Avondale Attic

JaninaRating, 5 stars3 weeks ago
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.
Guest favorite
Apartment in Lincoln Park
4.88 out of 5 average rating, 219 reviews

Lincoln Paradise– Steps to Park & Zoo!

JeanneRating, 5 stars3 days ago
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!!
Top guest favorite
Apartment in Bridgeport
4.98 out of 5 average rating, 56 reviews

Sunny Cozy Spacious Boho-Chic Condo in Bridgeport

JudyRating, 5 stars5 days ago
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!
Top guest favorite
Apartment in Lincoln Park
5 out of 5 average rating, 264 reviews

Explore Lincoln Park from a Polished Apartment

TomRating, 5 stars1 week ago
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

Guest favorite
Apartment in West Loop
4.96 out of 5 average rating, 27 reviews

Skyline Oasis: City & Lake Views

NatalieRating, 5 stars3 weeks ago
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!
Top guest favorite
Apartment in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars1 month ago
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.
Superhost
Apartment in Chicago
4.83 out of 5 average rating, 54 reviews

Rooftop HotTub As Seen On "Married At First Sight"

KimikoRating, 5 stars8 months ago
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!!
Superhost
Apartment in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars1 week ago
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.
Superhost
Apartment in West Loop
4.83 out of 5 average rating, 120 reviews

Penthouse Near Fulton: Skyline, Spacious

EmadRating, 5 stars4 days ago
Great place nice views , communication with host very smooth !
Superhost
Apartment in The Loop
4.69 out of 5 average rating, 49 reviews

Sentral 1 Bedroom Apt in South Loop Chicago

RichardRating, 5 stars2 weeks ago
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.
Top guest favorite
Apartment in Belmont Cragin
4.98 out of 5 average rating, 119 reviews

Belmont Pleasures - hot tub / arcade gaming room

AustinRating, 5 stars1 week ago
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.
Guest favorite
Apartment in Irving Park
4.92 out of 5 average rating, 36 reviews

2Bed 2Bath 15min to Wrigley with Parking& Balcony

AlexRating, 5 stars1 week ago
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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