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Vacation rentals in Pilsen

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Pilsen

  • Total vacation rentals

    Explore 110 vacation rentals in Pilsen

  • Nightly prices starting at

    Pilsen vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 4,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    110 of Pilsen vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pilsen rentals

  • 4.6 Average rating

    Pilsen stays receive an average rating of 4.6 out of 5 from guests

Top-rated vacation rentals in Pilsen

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
A cozy living area features a green sectional sofa arranged around a circular coffee table. A wall-mounted television displays a warm fireplace. Shelving holds decorative elements, while a window allows natural light to illuminate the space. The ceiling showcases wooden beams for added character.
Apartment in West Side
4.81 out of 5 average rating, 140 reviews

Charming retreat w/ fireplace

Experience the soul of Chicago in this unique, tranquil getaway nestled in the heart of historic Pilsen! Immerse yourself in the neighborhood's famous murals and vibrant culture. 🏠 The Space: Spacious & bright with a private bathroom for the main bedroom plus an in-unit washer/dryer. 📍 Pilsen Living: 🛒 5-min walk to Aldi 🌮 Steps to taco trucks & cozy bars 🍕 BYOB pizza nearby 🚶 Transit: 3-min walk to the Pink Line/Bus 🚗 15-min to Downtown/McCormick Place Check out my other listings!

Superhost
The exterior of a historic four-story building showcases intricate stonework and arched windows. Two blue doors with glass inserts serve as the main entrance, framed by a wooden porch that leads to the entrance. The surrounding greenery adds a touch of nature.
Loft in West Side
4.72 out of 5 average rating, 190 reviews

Studio with View of Skyline in Heart of Pilsen

Explore Pilsen and the beautiful City of Chicago in this unique Loft Style Studio apartment with a view of the Willis Tower and in the Heart of Pilsen. Apartment features a Roku TV with Wifi, private entrance, open layout, closet, bathtub with handheld shower head. 1 queen bed and a sofa bed couch, no kitchen but does have a fridge. Unit is on the 4th floor, no elevator. No Private Parking, just street parking only . Located near major transportation, Divvy Bike Station across the street.

Top guest favourite
Apartment in West Side
4.96 out of 5 average rating, 56 reviews

Quiet Pilsen Sunlit Apt W/D Queen Near Downtown

This lovely bright apt in the ❤️ of Chicago / Pilsen neighborhood ft. vintage decor & a welcoming vibe in a quiet, family-owned building. The 3rd FL apt is perfect for couples or friends, with easy access to transit, restaurants, grocery stores, local murals, & museums. Downtown is a short 15-minute drive. Amenities: Key less entry, in-unit W/D, fully equipped kitchen, & shared yard. The 1-BR apt sleeps two, with a queen air mattress available to accommodate up to four guests upon request.

Guest favourite
Apartment in West Side
4.94 out of 5 average rating, 34 reviews

Apartment in Chicago. Just 15 mins from downtown

Escape to your private sanctuary in Chicago near downtown. We have (2) charming one-bedroom apartments next door to each other. The perfect blend of comfort and convenience for your next getaway. A peaceful neighborhood, you'll find a bright and inviting living space, complete with comfortable sofas and smart TVs for relaxing evenings. The fully equipped kitchen has everything you need to whip up a delicious meal, whether it's a quick breakfast or a gourmet dinner. A safe space to unwind.

Guest favourite
Apartment in West Side
4.91 out of 5 average rating, 193 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.

Guest favourite
Apartment in West Side
5.0 out of 5 average rating, 12 reviews

Pilsen Prism: Sun-Drenched 3BR + Parking

Experience the ultimate Chicago stay in this sun-drenched Pilsen sanctuary. With massive floor-to-ceiling windows and an "urban treehouse" vibe, this modern 3BR/2.5BA duplex is a light-filled retreat for groups. Enjoy soaring ceilings, a sleek chef’s kitchen, and curated minimalist design. Rare bonus: 1 private parking spot included! Nestled in the heart of Pilsen’s world-class art and dining scene. Spacious, stylish, and perfectly located - your luminous urban escape starts here.

Guest favourite
Apartment in West Side
4.94 out of 5 average rating, 31 reviews

Great place in the Heart of Pilsen

"This apartment comfortably accommodates 4 adults with 2 bedrooms and 1.5 baths. There's space for 2 additional guests on an inflatable bed. The spacious main bedroom also features a dedicated workspace. Enjoy the beautiful outdoor area/porch that's assigned exclusively to this apartment. Conveniently located, you'll find CTA buses and the train station within walking distance, and you're just steps away from Thalia Hall and a vibrant selection of trendy restaurants and bars."

Guest favourite
A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.
Apartment in Bridgeport
4.93 out of 5 average rating, 244 reviews

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

Guest favourite
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 West Side
4.88 out of 5 average rating, 333 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.

Guest favourite
A spacious bedroom is featured, highlighted by a large bed with a decorative white coverlet. Two bedside lamps flank the bed, and a round mirror is mounted above the headboard. A soft area rug lies on the floor, and natural light enters through large windows.
Apartment in West Side
4.8 out of 5 average rating, 179 reviews

816 PLZN Penthouse| Rooftop| Garage Parking

Welcome to your stylish retreat in vibrant PILSEN! This modern apartment offers garage parking, a rooftop with stunning views of Willis Tower, and a cozy firepit for relaxing evenings. Explore the neighborhood's murals, visit local bars like Simones, and enjoy Sunday brunch at Duseks. Catch a concert at Thalia Hall or sing your heart out at karaoke bars nearby. Experience the best of art, food, and entertainment in PILSEN – book your stay now!

Guest favourite
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 West Side
4.95 out of 5 average rating, 130 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.

Guest favourite
A charming brick building features intricate stone detailing, complemented by bright orange doors. A secure iron fence encloses the entryway, with a well-maintained walkway leading to the entrance. Sunlight casts gentle shadows on the path, enhancing the welcoming appearance.
Apartment in West Side
4.89 out of 5 average rating, 371 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/

Popular amenities for Pilsen vacation rentals