Vacation rentals in Pilsen

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Top-rated vacation rentals in Pilsen

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Guest favorite

A cozy sleeping area features a neatly made bed with soft gray pillows and a decorative green bolster. A bedside lamp and a small plant add touches of comfort, while a piece of framed artwork hangs on the white wall above the bed.

Guest suite in Lower West Side

4.99 out of 5 average rating, 136 reviews

Cozy Hideout in Art Filled Chicago Neighborhood

Your private guest suite is newly renovated. You will have a private room with your own keypad entrance, thermostat and bathroom, T.V. with internet access, mini fridge, serving ware, coffee maker, fruit and yogurt in the fridge! We also have a toaster oven in case you want to warm up leftovers. You will only have access to your room, which is comparable to a short term stay hotel room, but way cooler. send a text or message me and I'll respond as soon as I can The Pilsen neighborhood got voted one of the 12 coolest neighborhoods in the world in 2018, according to Forbes magazine. There’s venues, studios, and bars booming with more culture all only blocks away. Uber / Lyft is a great way to get anywhere quick - usually a 15 min ride to downtown. Public transit options are the CTA El Train (Pink Line 18th stop is 0.7 mile walk from our house) or CTA Bus (18th & Racine stop is a block away). Once you’re at the transit stop both options take about a 20 - 30 minute to downtown. There are other bus lines nearby that take you other places (i.e. McCormick Place) - feel free to ask us for help when you arrive. Street parking is free in certain areas for those who are driving. Please message us and we’ll direct you where to park. We are a 20 minute cab ride from Midway International Airport and 40 minutes from O'Hare without heavy traffic, double these estimates if traffic is heavy (rush hour, accidents, etc).

Top guest favorite

The living area features an original tile floor complemented by green tin walls and ceiling. A brown leather sofa is positioned alongside wooden armchairs, and a circular coffee table occupies the center. A large mirror reflects light from the windows, enhancing the space's openness.

Apartment in Bridgeport

5 out of 5 average rating, 28 reviews

Al Capone Era Speakeasy 3 BRs

Located in Bridgeport, the geographic center of Chicago, this former Al Capone era speakeasy / tavern has been lovingly transformed into a 3 bedroom apartment. The amazing original tile floor, tin walls, and tin ceiling remain intact. Imagine the stories this place could tell! Bridgeport, one of the hottest neighborhoods in Chicago, is 15 minutes from downtown, 15 minutes from the beach, 5 minutes from Chinatown, and home to many restaurants, coffee shops, night life, Sox Park, and much more.

Superhost

A relaxing living space is presented with a large, colorful sofa adorned with various cushions. A wooden coffee table sits in the center, surrounded by soft lighting from lamps. Textured wall decor, a mirror, and a minimalist television add to the inviting ambiance.

Apartment in South Loop

4.92 out of 5 average rating, 12 reviews

Cozy East Pilsen Garden | Great Location!

Step into a warm and inviting space where eclectic design meets modern comfort. Nestled in East Pilsen - Chicago Art District we offer a California King bed in the main bedroom and a queen bed in a cozy bedroom nook separated by a curtain for a relaxed yet intimate vibe. Perfect Location! 7 minutes walk from Radius & short trips to Downtown, Chinatown (6 min.), Greektown, 12th Street Beach, Field Museum, Art Institute of Chicago, Sox Park, Buckingham Fountain, Willis Tower, Navy Pier etc.,

Superhost

A spacious bed layered with a colorful patterned blanket is positioned near large glass doors that open to a private deck. Sheer curtains frame the entrance, allowing natural light to fill the room while offering a view of the greenery and flowers on the deck.

Guest suite in South Loop

4.92 out of 5 average rating, 144 reviews

Entirely Private Suite - Urban Oasis - Pilsen/UIC

Pilsen - McCormick Place - Soldier Field - Thalia Hall - UIC - Chinatown - South Loop - Radius Welcome to a brand new, entirely private, spacious and peaceful oasis in Pilsen-UIC with a smartlock system and self check in. Central location near some of the hottest neighborhoods, restaurants, concert and tourism venues, and minutes from the Loop! Full bath with a luxurious spa shower, cable, wifi, flatscreen tv, refrigerator, iron, desk, coffeemaker, toiletries and a lovely private deck.

Guest favorite

A bright living area features high ceilings and large windows providing natural light. A striped sofa and a minimalist black chair are positioned around a glass coffee table, complemented by a decorative cowhide rug. Art pieces, including an abstract painting, add character to the space.

Loft in Little Italy

4.9 out of 5 average rating, 412 reviews

Pilsen Modernist, Creative, Lightfilled Loft

Take morning drinks through the sunshine-yellow room to the back porch, or watch light dance on translucent walls and glossy black and white hardwood floors. Eclectic design includes a mix of new and vintage furniture, and a collection of art and design books for guests to enjoy. This unit is owned by an artist couple who split their time between Tucson, AZ and Chicago. This is their personal unit when they're in Chicago. Come stay here to get away, be comfortable, relax, and be inspired.

Guest favorite

A cozy sleeping area is presented with a spacious bed dressed in dark bedding, accented by two patterned pillows and a green decorative pillow. A soft teal blanket and folded towels are placed at the foot of the bed, while a framed artwork hangs on the wall above.

Apartment in Lower West Side

4.89 out of 5 average rating, 36 reviews

Garden Apartment in Historic Pilsen Arts Area

This private garden unit is ideally located and well-equipped with everything you need for a comfortable homebase on your Chicago adventure. Come to Pilsen and experience one of Chicago’s most vibrant neighborhoods. With dozens of unique shops to explore, delightful coffee shops, Pilsen is a beating heart of arts and culture. Peruse charming streets filled with distinctive and historic architecture, admire beautiful street murals, and try one of Pilsen's many delicious taquerias.

Guest favorite

A cozy living area features a soft sectional sofa facing a low coffee table on a colorful area rug. Natural light filters through large windows, illuminating the modern kitchen area in the background, defined by sleek cabinetry and stainless-steel appliances.

Apartment in Chicago

4.98 out of 5 average rating, 57 reviews

Cozy Chicago Apartment next to the River

Conveniently located apartment next to the South Branch of the Chicago River and Park district Boathouse. On the second floor, with a stunning view of the skyline, stylish two-bedroom, two-bathroom apartment with high-speed internet. The Orange line is easily accessible on foot, and the Loop can be reached in about 15 minutes by car. If you'd rather stay in the immediate area, you may take a stroll along the river or head down the street to a charming gastro-tavern and restaurant.

Guest favorite

A vibrant living area features a red couch and a cozy accent chair. The kitchen is visible in the background, highlighted by sleek cabinetry and bar seating. Colorful beams adorn the ceiling, adding character to the open space, while large windows allow natural light to fill the room.

Loft in Lower West Side

4.93 out of 5 average rating, 42 reviews

18th St Cozy and Unique 2BR Loft

Stay in our colorful and comfy Loft. Located in Pilsen, also known as ‘Heart of Chicago’. You are in walking distance to an array of restaurants from street food to fine dining. Enjoy a show at the historical Thalia hall theatre or a night at the piano bar downstairs. You’re only a five minute drive from Chinatown, Greektown and Little Italy; and ten minutes from Millenium Park. Absolutely NO SMOKING in the apartment and inside of the building‼️ Absolutely NO PARTIES‼️

Guest favorite

A vibrant mural features a yellow spotted leopard among colorful flowers on a black background. The mural showcases bold shades of pink, orange, and green, enhancing the courtyard's lively character. The concrete path leads towards the mural, framed by a wrought iron fence and nearby planters.

Guest suite in Lower West Side

4.95 out of 5 average rating, 201 reviews

Casita Plzeň Guest Suite

Stay in the heart of one of the world’s coolest neighborhoods, as recognized by Forbes, in a Historic Chicago Worker’s Cottage from the 1800s. The Loop is just five stops away on the Pink Line. McCormick Place is a 20min trip, the hospital district is just 15 mins away, Soldier Field and the UC are a short Uber ride. The lakepath, only two miles from your doorstep. Experience Chicago like a local, with history, convenience, and adventure all in one unforgettable stay.

Guest favorite

A modern kitchen features sleek black cabinetry and appliances, complemented by a contrasting white countertop. Stylish stools are arranged around a small kitchen island. The wall is adorned with a framed painting, while decorative items are displayed on open shelves above the countertop.

Apartment in Lower West Side

4.87 out of 5 average rating, 280 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.

Top guest favorite

A green sofa is positioned in a bright living area, accompanied by a round coffee table. A decorative bowl and a potted plant sit atop the table, while a piece of wall art featuring a tree landscape adds character. Natural light enters through nearby windows.

Apartment in Lower West Side

4.99 out of 5 average rating, 243 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.

Guest favorite

A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.

Apartment in Lower West Side

4.92 out of 5 average rating, 66 reviews

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.