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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"

Jul 24 – 31

G$19,250 GYD per night

Apartment in West Town

4.96 out of 5 average rating, 263 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen w/ stainless appliances, excellent bathroom, shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID.

Nov 20 – 27

G$20,823 GYD per night

Apartment in Chicago

4.94 out of 5 average rating, 265 reviews

Cozy City Living-Near Downtown-Train-Food!

Experience the best of one of Chicago's favorite neighborhoods in this recently renovated, modern 2BR apartment. Perfect for couples, families, or small groups. Centrally located, minutes to downtown, CTA/L Pink Line train one block away. Free WiFi, cable, parking, in-unit front load washer/dryer, fresh towels & linens. Explore the vibrant community, delicious restaurants, and cultural venues. Book now for a comfortable and memorable stay in the heart of Pilsen!

Sep 9 – 16

G$35,455 GYD per night

Apartment in Pilsen Historic District

4.85 out of 5 average rating, 234 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.

Oct 2 – 9

G$15,899 GYD per night

Apartment in Pilsen Historic District

4.89 out of 5 average rating, 202 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.

Sep 23 – 30

G$50,872 GYD per night

Apartment in Chicago

4.98 out of 5 average rating, 132 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 20 – 27

G$30,505 GYD per night

Apartment in Pilsen Historic District

4.82 out of 5 average rating, 431 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 21 – 28

G$34,555 GYD per night

Apartment in Little Italy

4.98 out of 5 average rating, 199 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!

Jan 9 – 16

G$36,979 GYD per night

Apartment in Cicero

4.98 out of 5 average rating, 203 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.

Apr 25 – May 2

G$27,441 GYD per night

Apartment in Chicago

4.84 out of 5 average rating, 176 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.

Oct 25 – Nov 1

G$15,891 GYD per night

Apartment in Pilsen Historic District

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 20 – 27

G$22,845 GYD per night

Apartment in Bridgeport

4.98 out of 5 average rating, 171 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).

Sep 16 – 23

G$23,053 GYD per night

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Popular amenities for Pilsen, Chicago apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Apartment in Chicago

4.85 out of 5 average rating, 273 reviews

HUGE|3br/2ba/Near DT/Free Parking/WI-FI/Pilsen

Sep 23 – 30

G$28,958 GYD per night

Apartment in Chicago

4.89 out of 5 average rating, 300 reviews

Vintage Bridgeport Apartment

Jul 3 – 10

G$31,199 GYD per night

Apartment in Humboldt Park

4.98 out of 5 average rating, 108 reviews

Humboldt Park Loft

Sep 15 – 22

G$25,520 GYD per night

Apartment in Chicago

4.92 out of 5 average rating, 492 reviews

2BR Bursting w/ Character in Hip Logan Square!

Feb 15 – 22

G$21,540 GYD per night

Apartment in Chicago

4.81 out of 5 average rating, 192 reviews

In artistic Pilsen~Continental Breakfast~Near DWTN

Sep 27 – Oct 4

G$32,344 GYD per night

Apartment in West Town

4.98 out of 5 average rating, 221 reviews

Ukrainian Village Garden Retreat

Oct 24 – 31

G$38,360 GYD per night

Apartment in McKinley Park

4.85 out of 5 average rating, 259 reviews

Charming loft style suite

Sep 15 – 22

G$22,644 GYD per night

Apartment in Chicago

4.78 out of 5 average rating, 211 reviews

Heart of Chicago 2BD + Parking

Oct 26 – Nov 2

G$21,385 GYD per night

Private apartment rentals

Apartment in Chicago

4.9 out of 5 average rating, 257 reviews

Bright & Lofty Bucktown 1br

Jan 18 – 25

G$24,305 GYD per night

Apartment in Lincoln Square

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Jul 28 – Aug 4

G$23,108 GYD per night

Apartment in West Town

4.92 out of 5 average rating, 327 reviews

Bright, Modern Apartment in a Vintage Greystone

Mar 2 – 9

G$32,063 GYD per night

Apartment in Chicago

4.82 out of 5 average rating, 272 reviews

*Entire City Apartment 1 block to Train Park Free

Nov 4 – 11

G$18,493 GYD per night

Apartment in Forest Park

5.0 out of 5 average rating, 223 reviews

Like a Treehouse!

Sep 29 – Oct 6

G$23,407 GYD per night

Apartment in Chicago

4.93 out of 5 average rating, 186 reviews

Spacious & Clean Ukrainian Village 2 Bedroom!

Jan 30 – Feb 6

G$27,283 GYD per night

Apartment in Chicago

4.97 out of 5 average rating, 237 reviews

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

Feb 17 – 24

G$33,831 GYD per night

Apartment in Pilsen Historic District

5.0 out of 5 average rating, 7 reviews

Casita Plzeň First Floor

Jul 10 – 17

G$32,721 GYD per night

Apartment rentals with a hot tub

Apartment in West Town

4.88 out of 5 average rating, 394 reviews

Checkerboard Studio with Private Outdoor Hot Tub and Yard

Oct 24 – 31

G$38,133 GYD per night

Apartment in Near South Side

4.87 out of 5 average rating, 156 reviews

Stunning Panoramic Chicago Views & Free Parking

Apr 29 – May 6

G$82,541 GYD per night

Apartment in Berwyn

4.91 out of 5 average rating, 204 reviews

“Dream slice of urban homesteading.”

Sep 13 – 20

G$31,015 GYD per night

Apartment in West Loop

4.87 out of 5 average rating, 106 reviews

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

Dec 27 – Jan 3

G$162,909 GYD per night

Apartment in Logan Square

4.91 out of 5 average rating, 32 reviews

Luxe Suite + Spa House Retreat! Pets Welcome

Jan 18 – 25

G$32,636 GYD per night

Apartment in The Loop

5.0 out of 5 average rating, 7 reviews

The Downtown Oasis (2BD / 2BA)

Aug 30 – Sep 6

G$71,983 GYD per night

Apartment in West Rogers Park

4.86 out of 5 average rating, 21 reviews

Spacious Beautiful Condo

Oct 14 – 21

G$34,678 GYD per night

Apartment in Chicago

4.87 out of 5 average rating, 45 reviews

Spectacular Rooftop Getaway in Heart of City

Aug 25 – Sep 1

G$100,711 GYD 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
G$4,169 GYD before taxes and fees

Destinations to explore