Vacation rentals in Pilsen, Chicago

Guesthouse in Little Italy

A spacious living area features a comfortable black leather sofa and a distinctive black chair. Natural light filters through large windows, illuminating the mid-century cabinetry and vibrant area rug. Light-colored curtains frame the windows, and a circular coffee table sits at the center.

4.99 out of 5 average rating, 858 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

4.95 out of 5 average rating, 397 reviews

A modern living area features a dark leather sofa adorned with blue and cream cushions. A stylish coffee table with geometric design sits atop a decorative area rug. A large black and white photograph of a city skyline is displayed on the wall, complemented by a floor lamp and a side table.

Home in Pilsen

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

House is perfectly located within walking distance of Pilsen's best attractions. Home is furnished and newly renovated with the idea of making your stay as comfortable as possible. Walking distance from Thalia Hall and many other great restaurants and coffee shops. For your convenience there is a "corner store" steps from the home where you can purchase food and beverage items. The whole apartment is professionally cleaned after every guest no matter how many days they have stayed. Fresh sheets and towels are provided for all guests as well. Walking distance from local favorites: Simone’s, Honky Tonk BBQ, Dusek's/Punch House/Thalia Hall, 5 Rabanitos, Furious Spoon, S.K.Y and HaiSous. Located 2 miles South West of Downtown Chicago. Extremely close to South Loop and West Loop. Amenities: - Washer and Dryer (located in unit) - Granite counter tops - All new appliances - Tiled bathroom - Central Heat/AC - Private back deck - Closet space All access, full kitchen, washer and drier in apartment. Private entrance with Keyless entry. Available at any time, happy to answer any questions you may have. Interaction will be dictated by guests. This is a vibrant family neighborhood with character, art, great food, and culture. Walk to amazing restaurants, bars, and coffee shops, including local favorites Simone’s, Honky Tonk BBQ, 5 Rabanitos, Furious Spoon, S.K.Y, and HaiSous. Close to major Chicago highways: I-190: Kennedy Expressway I-290: Eisenhower Expressway I-55: Stevenson Expressway I-90/94: Chicago Skyway, Dan Ryan Expressway, Kennedy Expressway, Jane Addams Memorial Tollway Public transit easily accessible: CTA Bus #8, 18, 60 CTA Trains: Blue, Pink and Orange Lines Divvy Bike Rental Station one block away Permit Parking $6-10 dollar Uber to Downtown

4.99 out of 5 average rating, 124 reviews

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 Pilsen

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).

A cozy studio is captured, featuring a comfortable gray sofa and a light wooden coffee table. Open shelves display kitchenware and appliances, while a round area rug complements the warm wood flooring. Soft lighting is provided by a modern ceiling fixture in the neutral-toned space.

4.82 out of 5 average rating, 180 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"

A well-equipped kitchen features wooden cabinets and a stainless steel stove. Open shelving displays white dishware and cooking essentials. The space includes a sink with dish drying rack and a countertop with a toaster, creating a functional area for meal preparation.

4.95 out of 5 average rating, 149 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!

Guest suite in South Loop

An armoire is seen against a wall, featuring open doors revealing a mini fridge and microwave. A neatly stacked assortment of towels is visible above the mini fridge. A doorway to a bathroom is located on the right, showing hints of modern fixtures.

4.92 out of 5 average rating, 138 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.

4.9 out of 5 average rating, 394 reviews

A sunlit kitchen area with white cabinetry and stainless steel appliances is showcased. A bright yellow wall complements mid-century-style furniture, featuring a light blue chair. Large doors open to the balcony, allowing natural light to fill the space.

Loft in Little Italy

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.

A hallway is flanked by a green wall adorned with a neon sign that reads 'Chicago.' Light wood flooring leads to an open area featuring a kitchen and living space, illuminated by natural light from large windows with light curtains.

4.89 out of 5 average rating, 118 reviews

Unmatched Urban Retreat Close to 18th Strip & Loop

This stylish Airbnb in the very popular Pilsen neighborhood is perfect for small and large travel groups. There are 2 bedrooms with queen size beds, and the couch folds out for an additional sleeping area. The 2 full bathrooms will have everything you need to get ready to hit the town. The tall ceilings make this space for larger than life, and the unique décor gives this Airbnb a great urban feel. The fully equipped kitchen and updated appliances are perfect for those quiet nights in.

4.95 out of 5 average rating, 190 reviews

Guest suite in Pilsen

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.

An ornate entrance gate welcomes visitors with the phrase 'Bienvenidos a Pilsen,' crafted in bold lettering. The intricate ironwork frames the entrance, reflecting the vibrant character of the Pilsen neighborhood. Light filters through the transparent doors, hinting at the lively atmosphere beyond.

4.87 out of 5 average rating, 264 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.

A modern living area features a green velvet couch and a round wooden coffee table atop a patterned area rug. A television is positioned on a media console, with natural light coming through multiple windows. Artwork adorns the walls, adding character to the space.

4.99 out of 5 average rating, 231 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.

A long hallway features exposed wooden beams and a mix of brick and painted walls. A sleek black table and chairs are positioned to the left, with potted plants adding greenery. Soft lighting illuminates the space, leading to areas for relaxation and dining.

4.84 out of 5 average rating, 101 reviews

Charming retreat w/ fireplace

Take it easy at this unique and tranquil getaway. Bedroom has its own bathroom. Enough space for friends and family. Everything is steps away located the Pilsen neighborhood. Corner convenience store, byob pizza parlor, neighborhood bar, and taco truck. Checkout my other listings! -3 min walking distance to the train/bus -15 min driving distance downtown -15 min McCormick place -8 min uic pavilion

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Popular amenities for Pilsen, Chicago vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Pilsen, Chicago's top sights

National Museum of Mexican Art28 locals recommend

Guaranteed Rate Field44 locals recommend

Chinatown89 locals recommend

Other great vacation rentals in Pilsen, Chicago

Two wooden shelves are mounted against a white subway tile backdrop. A variety of glassware and ceramics are displayed, including six blue glasses and several green mugs. A small plant in a gold pot and a framed painting are positioned on the upper shelf.

4.86 out of 5 average rating, 22 reviews

Stylish Two Bedroom near Downtown Chicago

SusruthaRating, 5 stars2 weeks ago

Marc was very responsive and provided clear instructions. The interiors are clean and tasteful. It would be even better if there could be guaranteed parking right next to the property rather than street parking. Also - not a major issue and Marc does let us know about this in his communications, but windows in this ground floor property can't be opened.

A modern kitchen features white cabinetry and stainless steel appliances, including a refrigerator and gas stove. A central island with seating for two is highlighted by pendant lighting. Windows allow natural light to enhance the airy atmosphere, while a plant adds a touch of greenery.

Home in Pilsen

5 out of 5 average rating, 3 reviews

Gorgeous home, 3BR/2BA, Free Parking, Free Laundry

재홍Rating, 5 stars1 week ago

Samantha was a wonderful host—she was very responsive and proactive in resolving any difficulties I faced, always with kindness. The space itself was spacious and well-suited for a family stay. I especially appreciated how well the bed was maintained, with a comfortable mattress and clean bedclothes. I would definitely choose this place again next time I travel to Chicago. My sincere thanks to the host!

5 out of 5 average rating, 11 reviews

A well-equipped kitchen features modern cabinetry and a spacious granite countertop. Stainless steel appliances include a gas stove and microwave. A coffee maker and kettle are available for use. The area is illuminated by under-cabinet lighting, providing a clean and efficient space for meal preparation.

Apartment in Bridgeport

Bridgeport Garden Studio

AnnaRating, 5 stars3 weeks ago

Nice neighborhood, walking distance to Rate Field. Easy to access, with clear instructions. Quiet neighborhood. Overall would recommend for a quick visit to the area!

4.93 out of 5 average rating, 27 reviews

A map display illustrates the route from the apartment to downtown Chicago, highlighting the proximity with a travel time of nine minutes. Major streets and landmarks, including the University of Illinois Chicago and Chinatown, are labeled to enhance navigation and orientation.

Guest suite in Pilsen

Pilsen Chicago's Art District Apartment

CaitlinRating, 5 stars4 weeks ago

Amelia is super responsive and you rarely have to wait more than a few minutes to hear back from her. Her space is in a great area that’s super walkable. Lots of restaurants, bars, bookshops, thrift and vintage stores, cafes, and a cute community garden. The space is minimal but has all of the amenities you need. It was the perfect spot for a short weekend trip to see a concert down the street. We arrived on a sunny day in the 80s, and her AC unit wasn’t installed yet. She offered to bring a fan, and did so within minutes. With Midwest weather I totally understand why it wasn’t installed (the next day the high was 60). It’s a garden unit so it stays cool, and there is a cute little fireplace for extra heat if you need it (again, Midwest weather!). The area was super quiet at night, though we could hear a pet playing upstairs occasionally which was adorable. Free parking is easy to find, which is a huge bonus. Overall a great stay!

A modern kitchen space is showcased, featuring stainless steel appliances, including a microwave and stove. A glass dining table with orange velvet chairs is positioned in the foreground, accompanied by a floral arrangement in a clear vase. Light reflects off the smooth surfaces, creating a bright atmosphere.

5 out of 5 average rating, 5 reviews

Artsy Pilsen Apartment

MadelineRating, 5 stars2 weeks ago

We had the best time here! Truly felt so comfortable and safe which is hard to find for a girl group traveling alone. Beth stopped by and gave us recommendations that we loved, and we will 10000% be staying here next time! Convenient, clean, and beautiful!

An open-concept living area features a round dining table with four woven chairs at its base. Large windows offer ample natural light, adorned with elegant drapes. A cozy sofa is positioned nearby, complemented by a wall of exposed brick, adding warmth to the space.

4.9 out of 5 average rating, 10 reviews

Duplex Luxury Apartment with King Suite

LinaRating, 5 stars2 weeks ago

Really beautiful place in a great location! Space was exactly as the pictures and had comfy beds/furniture! Cris was also very quick to respond and helpful. Would definitely stay here again.

An outdoor space features a wooden deck under a colorful canopy of papel picado. A small dining table with two chairs is set up, accompanied by potted plants. A vibrant mural adds color to the backdrop, enhancing the cozy and artistic environment.

4.52 out of 5 average rating, 110 reviews

Heart of Pilsen

BrookeRating, 5 stars1 week ago

This is a perfect location right outside of the busy city. It was everything we needed!

A corner of a room is highlighted, featuring a round black dining table surrounded by four chairs. An area rug with abstract patterns in yellow and gray covers the wooden floor. Large windows with blinds provide natural light, while a piece of wall art adds a touch of decor.