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Apartment holiday 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

Guest favourite
Flat in Little Italy
4.95 out of 5 average rating, 43 reviews

Spacious Studio in Little Italy, Near West Loop

MoriahRating, 5 stars2 weeks ago
I loved this stay! It was in a great walkable area and not far from downtown Chicago. I would definitely stay again.
Top guest favourite
Flat in Little Italy
5 out of 5 average rating, 45 reviews

Style, comfort, and convenience

AshleyRating, 5 stars6 days 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 favourite
Flat in Bridgeport
5 out of 5 average rating, 23 reviews

Al Capone Era Speakeasy 3 BRs

TimRating, 5 stars4 weeks 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.
Superhost
Flat 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.
Guest favourite
Flat 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
Superhost
Flat 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.
Top guest favourite
Flat in Bridgeport
4.98 out of 5 average rating, 56 reviews

Sunny Cozy Spacious Boho-Chic Condo in Bridgeport

JudyRating, 5 stars4 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!
Guest favourite
Flat 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.

Private apartment rentals

Guest favourite
Flat in Avondale
4.97 out of 5 average rating, 162 reviews

Designer Avondale Attic

JaninaRating, 5 stars2 weeks ago
Just wonderful. That was one of the most beautiful accommodations I've ever been to. The apartment is totally lovingly furnished. Everything was super clean and tidy. There are even toothbrushes, toothpaste and a sleeping mask, if you need them. The kitchen is also super equipped with everything you need. The short walk to the metro was also very convenient. We would definitely come back.
Guest favourite
Flat in Lincoln Park
4.88 out of 5 average rating, 219 reviews

Lincoln Paradise– Steps to Park & Zoo!

JeanneRating, 5 stars2 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!!
Guest favourite
Flat 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.
Superhost
Flat in Bronzeville
4.9 out of 5 average rating, 107 reviews

Chicago Themed Garden Unit - Historic Bronzeville

ArnabRating, 5 stars1 month ago
Kendal is a superhost. The apartment is as described. Enjoyed staying at this apartment. Very near to supermarkets, McCormick convention centre and public transport. Highly recommend.
Top guest favourite
Flat in Lincoln Park
5 out of 5 average rating, 264 reviews

Explore Lincoln Park from a Polished Apartment

TomRating, 5 stars6 days 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.
Superhost
Flat 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.
Top guest favourite
Flat in Magnificent Mile
4.98 out of 5 average rating, 160 reviews

Elegant Suite in Gold Coast

MikeRating, 5 stars3 days ago
A perfect stay! Next time I am in Chicago, this will be my first choice. I "second" all the great things that everyone else has said. I was here for a multi-day conference at a very nearby hotel, and I am so glad I chose here over the host hotel. Wonderful staff, great communication! Top notch in every respect! Thank you!
Guest favourite
Flat in Near North Side
4.9 out of 5 average rating, 101 reviews

50th Floor Mag Mile Studio

SylvieRating, 5 stars2 weeks ago
This penthouse was so beautiful, with stunning views. The location was perfect- everything we needed was within walking distance. James and Jeri-Lou were very responsive and made the stay seamless. I would highly recommend for a weekend in Chicago!

Apartment rentals with a hot tub

Superhost
Flat in The Loop
4.92 out of 5 average rating, 49 reviews

The Areal Oasis

Sheyla MRating, 5 stars2 weeks ago
I absolutely fell in love with this place! The amenities here alone will have you staying in for days because there is so much to do! The views are breathtaking and waking up to the view of the city will never get old! Everything you need is at a walkable distance and with the target right next door you will never be in need of a thing! Stephanie is a great host and very, very easy going. Will be coming back for sure!
Superhost
Flat in West Rogers Park
4.85 out of 5 average rating, 79 reviews

Spacious Beautiful Condo

SophiaRating, 5 stars6 days ago
We came for our daughter’s graduation and stayed a few extra days to tour the city. This place was perfectly located for both occasions. It was much more spacious than we expected, and everything was very clean. We especially appreciated the fresh towels and beddings. Our only wish is that the beds were a bit larger, especially the double bed, which would be more comfortable for a couple if it were at least a queen size. That said, the beds were very comfortable. Overall, we had a wonderful stay - definitely one of our best Airbnb experiences!
Guest favourite
Flat 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!
Superhost
Flat 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!!
Top guest favourite
Flat 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
Flat 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
Flat in West Loop
4.83 out of 5 average rating, 120 reviews

Penthouse Near Fulton: Skyline, Spacious

EmadRating, 5 stars3 days ago
Great place nice views , communication with host very smooth !
Superhost
Flat 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.

Quick stats about flat rentals in Pilsen, Chicago

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹2,579 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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