Family-friendly vacation rentals in Pilsen

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.

4.82 out of 5 average rating, 132 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!

4.95 out of 5 average rating, 152 reviews

A bright living area features a comfortable gray sofa with decorative pillows, a round coffee table, and large windows overlooking a private outdoor space. Light wood flooring complements the modern kitchen area, which includes sleek bar stools and stainless steel appliances.

Apartment in West Loop

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!

4.93 out of 5 average rating, 123 reviews

A comfortable living area is highlighted by a light gray sectional sofa and a white coffee table, placed on a textured gray rug. The kitchen area is visible in the background, featuring wood cabinets and modern appliances, enhancing the space's functionality.

Apartment in Bridgeport

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

A colorful mural featuring a heart symbol is prominently displayed. The heart is surrounded by a sunburst pattern and flanked by vibrant decorative elements in various colors. The word 'PILSEN' is written across the heart in a bold font, emphasizing the community's identity.

4.85 out of 5 average rating, 224 reviews

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

Guest suite in South Loop

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.

4.93 out of 5 average rating, 157 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.

A modern kitchen features stainless steel appliances, a granite countertop, and sleek white cabinetry. Two high stools are positioned at the island, providing additional seating. Ample natural light enters through a window, illuminating the clean lines and functional layout of the space.

4.94 out of 5 average rating, 334 reviews

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.

A newly remodeled kitchen features modern white cabinetry and a patterned backsplash. A black refrigerator and stove are positioned alongside a dining table with high stools. Natural light illuminates the space through a window covered by light curtains, adding to the inviting atmosphere.

4.84 out of 5 average rating, 173 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.

4.95 out of 5 average rating, 167 reviews

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Bridgeport

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

4.95 out of 5 average rating, 200 reviews

A bright living area features a plush blue sofa adorned with yellow and patterned cushions. Decorative artwork graces the walls, and a round area rug lies beneath a modern coffee table. A dining table is positioned in the background, surrounded by chairs.

Home in Bridgeport

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.

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.

4.82 out of 5 average rating, 157 reviews

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!

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.

4.95 out of 5 average rating, 112 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.

Apartment in Little Italy

The kitchen features wooden cabinetry with a black countertop and stainless steel appliances. A gas stove is positioned centrally, while decorative plants are arranged atop the counters. The flooring consists of white tiles, and a red area rug adds a pop of color.

4.78 out of 5 average rating, 230 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.

Popular amenities for Pilsen family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 55 reviews

A rooftop hot tub is showcased against a panoramic view of the Chicago skyline. The tub features jets and a spacious seating area. Clear blue skies and distant city buildings enhance the relaxing atmosphere, inviting guests to unwind while enjoying the urban scenery.

Condo in Wicker Park

Luxury Condo w/ HOT TUB and Stunning Roof Top Deck

4.87 out of 5 average rating, 94 reviews

A spacious living room features a rich blue accent wall and mid-century modern furniture. Two armchairs and a plush sofa are arranged around a low coffee table. A television is mounted on the wall, complemented by decorative wall art. Natural light fills the room.

Home in Westchester

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

Condo in Ukrainian Village

The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.

4.98 out of 5 average rating, 113 reviews

Ukrainian Village 3BR/3BA • Private Patio, Parking

5 out of 5 average rating, 18 reviews

A warm living room setting showcases two comfortable armchairs and a wooden coffee table at the center. Built-in bookshelves line the walls, displaying personal items and décor. Soft lighting from a nearby lamp enhances the cozy ambiance, while large windows allow for natural light.

Home in Oak Park

Elegant 4bedroom, 5 bathroom home on a great block

4.76 out of 5 average rating, 110 reviews

Apartment in Chicago

Super Paradise+65 Amenities*Downtown 15 Min

5 out of 5 average rating, 21 reviews

A spacious covered patio area features a dining table surrounded by six upholstered chairs, a high-top bistro table with two stools, and a cozy seating arrangement. A decorative plant sits in the center of the dining table, and an outdoor grill is positioned nearby.

Home in Evergreen Park

Stunning modern home with a lovely backyard

4.86 out of 5 average rating, 177 reviews

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

The Spa of Downtown Whiting

4.92 out of 5 average rating, 48 reviews

Home in Wrigleyville

*New* Luxury Wrigley Penthouse, Free Parking

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 338 reviews

The living area features exposed brick walls and hardwood floors, with an arrangement of seating including a red armchair and a cozy sofa. A glass coffee table sits on a plush area rug. A wall-mounted flat-screen TV is present, alongside indoor plants and decorative elements.

Condo in Lincoln Park

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

4.94 out of 5 average rating, 120 reviews

A round dining table is set with blue dishware and a floral centerpiece. Four light-colored chairs surround the table, placed on a patterned area rug. Natural light is visible through two softly shaded windows, and a tall green plant adds a touch of greenery to the room.

Apartment in Beverly

Beverly Cottage Loft

4.95 out of 5 average rating, 256 reviews

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

Apartment in Lake View

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

4.95 out of 5 average rating, 133 reviews

A modern living space features a sleek kitchen island with a sink, surrounded by light wood flooring. Large windows invite natural light, illuminating a comfortable gray sofa and a dining table with black chairs. A vibrant wall art piece adds color to the room.

Condo in Lincoln Park

NEW luxury Old Town 1-Bedroom condo

4.98 out of 5 average rating, 212 reviews

A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.

Home in Berwyn

RetroModern Bungalow | pet friendly | free parking

4.89 out of 5 average rating, 152 reviews

Apartment in Chicago

Fun 2BR with Retro Arcade 10 Mi Downtown Sleeps 6

Guest suite in Portage Park

A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.

4.95 out of 5 average rating, 162 reviews

Eddy Street Upstairs Apartment

4.75 out of 5 average rating, 144 reviews

A four-story brick house with a peaked roof is highlighted. The entrance features a set of stairs leading up to a glass door, framed by large windows on the lower floors. A manicured hedge runs along the front of the property, with a gentle pathway visible beside the structure.

Home in Bridgeport

Chicago's Bridgeport Huge 4 Story w/Garage Parking

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 74 reviews

The open living area features a spacious sectional sofa with soft green upholstery, complemented by a round coffee table. Large windows provide natural light, showcasing views of the surrounding cityscape. The modern kitchen, visible in the background, includes stainless steel appliances and bar seating.

Apartment in The Loop

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool

4.95 out of 5 average rating, 132 reviews

A bright living area features large windows that offer city views. Comfortable seating arrangements include a pair of teal sofas and a wooden armchair. A coffee table sits at the center on a soft area rug, accompanied by a flat-screen TV mounted on a nearby wall.

Condo in Evanston

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

4.95 out of 5 average rating, 64 reviews

A spacious living area showcases floor-to-ceiling windows offering skyline views. Modern furniture includes a light-colored sofa and two black chairs. A round table with four chairs occupies one corner, while a leafy plant adds a touch of nature. Sunlight brightens the airy room.

Apartment in West Loop

West Loop PH: Unmatched Views & Private Deck

Condo in Elk Grove Village

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

4.93 out of 5 average rating, 111 reviews

Just remodeled apartment close to airport and mall

4.95 out of 5 average rating, 22 reviews

A comfortable living area is presented with two soft armchairs and a light-colored couch. A media console houses a Roku TV, while a decorative electric fireplace offers warmth. Artwork adorns the walls, and natural light enters through a window with blue curtains.

Townhouse in Forest Park

Forest Park Oasis - Dog Friendly - Parks - the "L"

4.75 out of 5 average rating, 290 reviews

A bright living area features a comfortable gray sofa and two modern chairs set around a round coffee table. Large windows provide expansive views of the city, while greenery adds a touch of nature to the space. The warm lighting creates a welcoming ambiance.

Apartment in The Loop

Stunning 3BR Penthouse in the Loop | Roof Deck

Apartment in Downtown Chicago

A rooftop pool area is shown, featuring a clear blue pool surrounded by lounge chairs in red and neutral tones. Sunlight reflects off the water, and tall buildings are visible in the background, contributing to a lively urban atmosphere.

4.91 out of 5 average rating, 114 reviews

Professional's Playground (Fitness Center • Sauna)