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Apartment vacation rentals in Pilsen, Chicago

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Top-rated apartment rentals in Pilsen, Chicago

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Apartment in Chicago

4.84 out of 5 average rating, 130 reviews

Perfect Private Getaway in Perfect Pilsen

This quiet and cozy studio in Pilsen is the perfect place to rest your head after a long day of exploring the Windy City. With so much to do in the area and easy access to public transit, you won't run out of ways to spend your time! Close to Chinatown, the United Center, and the Medical District, and downtown is a quick train ride away on the Pink Line. Relax in this thoughtfully designed space, perfect for couples or business travelers. Book today! Please note: ceiling height is about 6'3"

Oct 8 – 15

R2,980 ZAR per night

Apartment in Pilsen Historic District

4.85 out of 5 average rating, 233 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond.

Aug 15 – 22

R1,422 ZAR per night

Apartment in Pilsen Historic District

4.89 out of 5 average rating, 201 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

Aug 22 – 29

R4,486 ZAR per night

Apartment in Chicago

4.98 out of 5 average rating, 129 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Jul 9 – 16

R2,578 ZAR per night

Apartment in Chicago

4.9 out of 5 average rating, 154 reviews

Spacious unique artist's home in Pilsen

Spacious 2 BR, 2nd floor in the wonderful Pilsen neighborhood *Pandemic Note: I am very concerned about keeping a safe environment for my guests and myself. My cleaning protocols exceed even Airbnb’s enhanced guidelines. 2.5 m. To downtown 1.6 m. To McCormack place Just 4 blocks to CTA station This is not a luxury loft, it is a hand crafted, rustic artist’s space with an open floor plan Bear in mind this building Dates to 1879. (charm?)

Sep 13 – 20

R3,722 ZAR per night

Apartment in Pilsen Historic District

4.82 out of 5 average rating, 429 reviews

Eclectic Artist Designed Sanctuary Heart of Pilsen

Start the day with a soothing cup of tea or Nespresso on the front stoop in the morning sunshine. White hardwood floors combine with mismatched artwork, glossy houseplants, and a classic leather Chesterfield for restorative afternoon naps. This apartment is owned and designed by an artist/musician and a philosopher. It is solely used for AirBnb guests, so it will truly feel like your own space. Come stay to get away, relax, and be inspired!

Oct 1 – 8

R3,118 ZAR per night

Apartment in Little Italy

4.98 out of 5 average rating, 198 reviews

Spacious 2BR on Quiet St - Free Park/Late Checkout

2 bedroom, 1 bathroom apartment, located just off Taylor Street in the heart Little Italy! Views of the Sears Tower from the front yard. Safe and lively neighborhood, packed with diverse restaurants, cafes, bakeries, parks, etc. all just a short walk from the apartment! Nearby West Loop also packed with trendy shops and amazing dining spots. Flat screen TV in every room, In-unit laundry, patio space, coffee/tea provided. 1pm check out!

Dec 24 – 31

R3,822 ZAR per night

Apartment in Cicero

4.98 out of 5 average rating, 201 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Dec 11 – 18

R2,346 ZAR per night

Apartment in Chicago

4.84 out of 5 average rating, 175 reviews

The Cottage

Nice cozy and welcoming place. Easy access to public transportation. 10 to 15 minutes from downtown, museums, Sox and Bulls stadiums. Located in the colorful and lively neighborhood of Pilsen and close to Little Italy. Smart devices installed for easy check-in and safety (extremely accurate and sensitive smoke detector warning all occupants of possible problems). Guest wifi included with some feel home amenities.

Sep 25 – Oct 2

R1,442 ZAR per night

Apartment in Chicago

4.89 out of 5 average rating, 243 reviews

Modern

Welcome to Pilsen, the neighborhood I have been living for 20 years! It is really cool and artsy. Forbes Magazine named the Pilsen neighborhood as one of the 12 coolest neighborhoods in the world. https://www.nbcchicago.com/blogs/worth-the-trip/Chicago-Neighborhood-Named-Among-Coolest-in-World-by-Forbes-486702851.html https://chicago.suntimes.com/news/pilsen-chicago-forbes-coolest-neighborhoods/

Oct 16 – 23

R2,061 ZAR per night

Apartment in Bridgeport

4.98 out of 5 average rating, 170 reviews

Bridgeport Garden Apartment

Enjoy a peaceful stay at this colorful, creative, artsy and relaxing garden unit apartment in the heart of Bridgeport. Located a few blocks away from Bridgeport's best bars and restaurants. This unit is good for couples, solo adventurers, business travelers and families (with kids). Street parking is free, and I’m readily available via phone or in person (I live a few minutes away).

Oct 3 – 10

R2,080 ZAR per night

Apartment in Pilsen Historic District

4.84 out of 5 average rating, 105 reviews

Spacious 2BR near downtown Chicago

This ample apartment is located less than two blocks from a main train station (pink line). It is in one of the most up and coming, lively, and full of diversity neighborhoods in the city. It is a 10-15 min drive downtown. For a mile down 18th street, there are endless shops, bars, restaurants, and other small businesses. The address can be provided via inquiry

Jun 24 – Jul 1

R3,262 ZAR per night

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Popular amenities for Pilsen, Chicago apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Apartment in Bridgeport

4.89 out of 5 average rating, 300 reviews

Vintage Bridgeport Apartment

Jul 6 – 13

R2,727 ZAR per night

Apartment in Chicago

4.85 out of 5 average rating, 258 reviews

Charming loft style suite

Sep 13 – 20

R2,076 ZAR per night

Apartment in Chicago

4.91 out of 5 average rating, 186 reviews

Lovely City Apartment Near Downtown-Food-Train!

Sep 27 – Oct 4

R3,078 ZAR per night

Apartment in West Town

4.96 out of 5 average rating, 262 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Mar 20 – 27

R1,929 ZAR per night

Apartment in Humboldt Park

4.98 out of 5 average rating, 107 reviews

Humboldt Park Loft

Oct 14 – 21

R2,303 ZAR per night

Apartment in West Town

4.98 out of 5 average rating, 219 reviews

Ukrainian Village Garden Retreat

Oct 25 – Nov 1

R3,473 ZAR per night

Apartment in Chicago

4.81 out of 5 average rating, 192 reviews

In artistic Pilsen~Continental Breakfast~Near DWTN

Jan 30 – Feb 6

R2,953 ZAR per night

Apartment in Chicago

4.89 out of 5 average rating, 473 reviews

iKlektik House Chicago / Robin

Dec 28 – Jan 4

R2,580 ZAR per night

Private apartment rentals

Apartment in Lincoln Square

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Jul 13 – 20

R2,172 ZAR per night

Apartment in Chicago

4.88 out of 5 average rating, 160 reviews

Bright, Gorgeous Apt Private Parking available

Jan 16 – 23

R2,666 ZAR per night

Apartment in Chicago

4.83 out of 5 average rating, 139 reviews

Modern, Spacious 3BR Apt Minutes to Downtown!

Sep 4 – 11

R2,919 ZAR per night

Apartment in Chicago

4.83 out of 5 average rating, 160 reviews

Chicago Vintage Home

Aug 13 – 20

R2,157 ZAR per night

Apartment in Near West Side

4.81 out of 5 average rating, 270 reviews

The Banksy-Greystone Rooftop Firepit United Center

R1,932 ZAR per night

Apartment in Chicago

4.97 out of 5 average rating, 236 reviews

Stylish First Flr. Studio. Best Location Division+Hermitage.

Feb 19 – 26

R3,081 ZAR per night

Apartment in Chicago

4.98 out of 5 average rating, 297 reviews

Redesigned Lower Level Studio in Historic Building

Oct 3 – 10

R2,800 ZAR per night

Apartment in Wicker Park

4.95 out of 5 average rating, 255 reviews

Heart of Bucktown

Jul 20 – 27

R2,383 ZAR per night

Apartment rentals with a hot tub

Apartment in Chicago

4.88 out of 5 average rating, 393 reviews

Checkerboard Studio with Private Outdoor Hot Tub and Yard

Oct 9 – 16

R3,441 ZAR per night

Apartment in Chicago

4.87 out of 5 average rating, 156 reviews

Stunning Panoramic Chicago Views & Free Parking

Apr 20 – 27

R7,448 ZAR per night

Apartment in Berwyn

4.91 out of 5 average rating, 202 reviews

“Dream slice of urban homesteading.”

Oct 2 – 9

R2,873 ZAR per night

Apartment in West Loop

4.87 out of 5 average rating, 106 reviews

Cloud9 |XL Penthouse+Movie Theater+Gym |The Harper

Mar 1 – 8

R14,427 ZAR per night

Apartment in Chicago

4.9 out of 5 average rating, 30 reviews

Luxe Suite + Spa House Retreat! Pets Welcome

Mar 11 – 18

R2,964 ZAR per night

Apartment in Chicago

5.0 out of 5 average rating, 6 reviews

The Downtown Oasis (2BD / 2BA)

Jan 14 – 21

R4,630 ZAR per night

Apartment in Chicago

5.0 out of 5 average rating, 10 reviews

Lake, City, & River View Condo

Jul 9 – 16

R6,145 ZAR per night

Apartment in Chicago

5.0 out of 5 average rating, 17 reviews

Spacious Beautiful Condo

Oct 14 – 21

R3,129 ZAR per night

Quick stats about apartment rentals in Pilsen, Chicago

Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
R376 ZAR before taxes and fees

Destinations to explore