Holiday houses in Pilsen

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!

Perfect Spot & Spacious 2BR+2BA | Mapletree Suites

Welcome to Mapletree Suites! Our stylish, clean, and contemporary 2 bed+2 bath suites are located in a boutique building in Chicago’s booming West Loop neighborhood. Keyless entry, blazing fast WiFi, bright white linens, in-unit laundry, 10ft ceilings, balconies, Italian cafe, host on-site, plus much more! Steps from Target store, parks/athletic field, CTA, and close to United Center, world-class restaurants, loop/lakefront, Med District, UIC, corporate offices and highway network. Book today!

Prime Bridgeport – McGuane Park

Located by Halsted Orange Line in Bridgeport, our Airbnb has is CENTERED around all the action in the neighborhood; surrounded by Grocery Stores, Fast Food, Drug Stores, Restaurants, and Iconic Parks. With a short commute to the Loop, UIC, Chinatown, we are especially sustainable for longer-term tenants! Enjoy the luxury of firm memory-foam mattresses and pillows and High-speed Internet, Central Heat and A/C and unlimited complimentary coffee for an amazing stay! 1 Queen Bed 1 Full Bed

Downtown & UC Nearby · Transit at Your Door

•Steps from the Damen Pink Line •Minutes to downtown Chicago via car or train •Easy access to major expressways I‑290 and I‑55 •Near major attractions like the United Center/Chinatown/Greektown/UIC/ West Loops nightlife and the Medical District •Vibrant cultural neighborhood - experience Pilsen’s rich art scene and authentic local dining •Ceiling height approx. 6’3” - please keep in mind when reserving •Memory Foam mattress •Guests must be 25+, have a verified account, and positive 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.

Lovely Stay Near Downtown+Parking +Train+Dining

Experience one of the best neighborhoods in Chicago. Centrally located, near downtown, CTA/L Pink Line train is one block away, highways nearby. This centrally located 2BR Hidden Gem is perfect for couples, families, or small groups. Free WiFi, parking, cable, in-unit washer/dryer, fresh linens and towels. Explore the vibrant neighborhood, art, murals, delicious food, and cultural venues Pilsen is known for. Pilsen is our home and we do our best to make your stay comfortable and memorable.

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.

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."

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. The property has a parking slab in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions you may have before booking. NO CHORES! Hot tub 5-6 Person Spa

Cozy Bright Quiet Boho-Chic House in Bridgeport

Kick back & relax in your home away from home in our modern, quaint, cozy & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & playful artwork, the coach house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Halsted Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Little Italy/UIC 3 bdrm, 2.5 bath Condo

Revel in your Chicago stay at this comfortable 3 bedroom, 2400 square foot duplex. This clean, spacious and cozy home sleeps up to 11 people. Enjoy two common living spaces and a fully equip kitchen, excellent for whipping up your favorite meals. This unit is a perfect space for multiple couples, a big friend trip or a family stay. You know they say it's all about location and this space gives you easy access to many of Chicago's most favorite attractions.

816 PLZN Penthouse| Rooftop| Indoor 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!