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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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Rental unit in Chicago

4.82 out of 5 average rating, 156 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"

Rental unit in Chicago

4.96 out of 5 average rating, 124 reviews

Cute, Clean, Cozy Apartment in Pilsen

Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

Rental unit in Bridgeport

4.96 out of 5 average rating, 111 reviews

The Photographers' Place

Tina and Kevin are your hosts for this Vintage cozy 600 sq. ft. apartment. 1st floor. Plenty of light. City living in established Bridgeport Neighborhood. Convenient location to McCormick Place (2miles), WinTrust Arena, Downtown, Chinatown, UIC, IIT, Soldier Field and Sox Park for baseball fans. Art, music, restaurant, brewery within walking or short bus ride. Grocery, Walgreens, CVS, Restaurants, Dunkin Donuts, Starbucks, 1 block away. We're only a phone call or text away.

Rental unit in Pilsen Historic District

4.84 out of 5 average rating, 111 reviews

Pilsen Blue Door

Beautiful, spacious, and super cozy 3 bedroom apartment in the heart of Pilsen if your looking for that at home Chicagoan feeling this is the place for you. Newly remodeled apartment featuring a large dining room, brand new kitchen, and bathroom. Experience living in one of Chicago’s most colorful communities, rich in history and culture. Not only is this apartment less than 9 minutes from downtown Chicago, you are walking distance to some of the best restaurants in Pilsen.

Rental unit in Pilsen Historic District

4.84 out of 5 average rating, 274 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.

Rental unit in Pilsen Historic District

4.86 out of 5 average rating, 228 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.

Rental unit in Chicago

4.98 out of 5 average rating, 180 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.

Rental unit in Pilsen Historic District

4.82 out of 5 average rating, 465 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!

Rental unit in Little Italy

4.98 out of 5 average rating, 221 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!

Rental unit in McKinley Park

4.86 out of 5 average rating, 293 reviews

Charming loft style suite

Original loft style 2nd floor apartment with private entrance. Thoughtfully furnished two bedrooms with a queen bed in each room. Plus a build in king size tatami in family room. A eat-in kitchen is convenient for basic warm up/cooking. There is a mini fridge, coffee maker and microwave. 10-20 Minutes drive to Loop, Museum Campus, Mc Cormick Place, Illinois Medical District, Soldier Field, White Sox& United Center.

Rental unit in Chicago

4.85 out of 5 average rating, 201 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.

Rental unit in Pilsen Historic District

4.8 out of 5 average rating, 208 reviews

In artistic Pilsen~Continental Breakfast~Near DWTN

Located in the artistic town of Pilsen; minutes away from downtown Chicago, Lake Shore drive, Shedd aquarium, United Center, UIC Pavilion and McCormick Place. Great and convenient location. Walking distance from CTA #60 bus-stop and pink line to downtown. Enjoy charming first floor, full kitchen, & bathroom. Also includes continental breakfast for first day of your stay and street parking with permit.

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Popular amenities for Pilsen, Chicago apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Rental unit in Wicker Park

4.96 out of 5 average rating, 118 reviews

Spacious Studio w/Balcony in Bucktown/Wicker Park

Rental unit in Chicago

4.91 out of 5 average rating, 102 reviews

Ground-Level Speakeasy: 1BR-1.5BA Near Everything!

Rental unit in Logan Square

4.96 out of 5 average rating, 414 reviews

King Bed, Huge Spa Shower, Dining Destination

Rental unit in The Loop

4.92 out of 5 average rating, 151 reviews

Spacious 1-bedroom South Loop Loft I Sleep 5

Rental unit in Logan Square

4.86 out of 5 average rating, 516 reviews

Logan Square Studio

Rental unit in Wicker Park

4.96 out of 5 average rating, 130 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Rental unit in Berwyn

4.91 out of 5 average rating, 325 reviews

Private apartment with retro vibe

Rental unit in Whiting

4.84 out of 5 average rating, 141 reviews

NEW! |Studio Apartment Whiting IN, United States#2

Private apartment rentals

Rental unit in Ukrainian Village

4.9 out of 5 average rating, 505 reviews

iKlektik House Chicago / Robin

Rental unit in Lincoln Park

4.84 out of 5 average rating, 250 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

Rental unit in Bridgeport

4.9 out of 5 average rating, 79 reviews

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

Rental unit in Lincoln Park

4.96 out of 5 average rating, 108 reviews

Elegant Depaul Apt on Jonquil Park

Rental unit in Chicago

4.88 out of 5 average rating, 78 reviews

Charming retreat w/ fireplace

Rental unit in Chicago

4.8 out of 5 average rating, 35 reviews

Cozy Pilsen Apartment

Rental unit in Little Italy

4.99 out of 5 average rating, 247 reviews

Modern+Spacious Inn Little Italy Near W Loop W/PKG

Rental unit in Chicago

4.99 out of 5 average rating, 182 reviews

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

Apartment rentals with a hot tub

Rental unit in West Loop

4.81 out of 5 average rating, 69 reviews

Quiet but in the Heart of City walk Everywhere

Rental unit in The Loop

4.87 out of 5 average rating, 30 reviews

The Areal Oasis

Rental unit in West Rogers Park

4.88 out of 5 average rating, 49 reviews

Spacious Beautiful Condo

Rental unit in West Loop

5 out of 5 average rating, 20 reviews

Skyline Oasis: City & Lake Views

Rental unit in Chicago

4.85 out of 5 average rating, 53 reviews

Private Rooftop Views from Penthouse Suite

Rental unit in Streeterville

5 out of 5 average rating, 21 reviews

Lake, City, & River View Condo

Rental unit in Belmont Cragin

4.99 out of 5 average rating, 73 reviews

Belmont Pleasures - hot tub / arcade gaming room

Rental unit in Roseland

4.94 out of 5 average rating, 48 reviews

420 friendly apt with 2 queens,1full roller,1 twin

Quick stats about apartment rentals in Pilsen, Chicago

Total rentals
40 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
2.2K 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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