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Family-friendly vacation rentals in West Loop

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in West Loop

  • Total vacation rentals

    Explore 230 vacation rentals in West Loop

  • Nightly prices starting at

    West Loop vacation rentals start at $113 CAD per night before taxes and fees

  • Verified guest reviews

    Over 14,430 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 110 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wifi availability

    230 of West Loop vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across West Loop rentals

  • 4.8 Average rating

    West Loop stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in West Loop

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favourite
A cozy living area features a brown leather sofa, light green armchairs, and a round wooden coffee table. A wall-mounted television is positioned above an area rug. Natural light filters through large windows dressed in sheer white shades, creating a bright ambiance.
Apartment in West Town

West Town 1-Bedroom Full Remodel

Located in the heart of West Town, this 1-bedroom, 1-bath comes equipped with a queen sofa bed and comfortably sleeps 4, plus an in-unit washer/dryer for your convenience. Remodeled in 2023, this stunning unit with 9ft ceilings in a Victorian building is footsteps away from all the amazing bars and restaurants Chicago Ave has to offer. Known for its array of multicultural cuisines, this strip offers everything from Korean fine dining to New Mexican brunch, and is near Chicago’s best attractions!

KitchenIndoor spacesDecor

4.98 out of 5 average rating, 123 reviews
Top guest favourite
A bright living area features a spacious sectional sofa, accent chairs, and a round coffee table. Large windows allow natural light to fill the space. A colorful wall art piece adds a vibrant touch, while decorative plants enhance the inviting atmosphere.
Apartment in West Loop

Clean & Best Location 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!

FamilyIndoor spacesLaundry

4.94 out of 5 average rating, 154 reviews
Top guest favourite
Apartment in West Loop

Fulton House #1 (2bd/ 1ba)

Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced apartment has the business-travel amenities you want: ultra speed wifi, work stations, top tier dining options within steps of the front door, Nespresso coffee, bottled water, washer/dryer. First-come parking next door: $20/nt or $200/mo.

KitchenIndoor spacesHeating

4.94 out of 5 average rating, 121 reviews
Guest favourite
The spacious open-concept living area features a modern kitchen with a central island and bar seating. A cozy seating arrangement includes a black leather chair and a circular coffee table. Natural light floods the room through the overhead circular skylight, enhancing the inviting atmosphere.
Loft in West Loop

Luxury Penthouse Loft - Heart of Fulton Market

NEW PENTHOUSE LOFT IN FULTON MARKET! Enjoy your own private luxury loft in Chicago's bustling Fulton Market-the city's center of main nightlife, restaurants and cultural scene. This 3,500 square foot penthouse features 12 foot open lofted ceilings, a dedicated elevator entrance, free onsite garage parking, 5 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

KitchenIndoor spacesWifi

4.86 out of 5 average rating, 177 reviews
Top guest favourite
The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.
Apartment in West Town

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

KitchenFamilyParking

4.97 out of 5 average rating, 637 reviews
Superhost
A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.
Apartment in Downtown Chicago

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

KitchenIndoor spacesAccess

4.81 out of 5 average rating, 1055 reviews
Top guest favourite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Apartment in Lincoln Park

Explore Lincoln Park from a Polished Apartment

A bright, cozy, large studio in the heart of Lincoln Park! You enter with a keypad code which we give you a few days prior to your stay. You are steps away from Armitage Ave. and Halsted St. for walkable grocery stores, shops, restaurants and cafes, plus Red and Brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment with free residential parking stickers or an onsite garage space for $25/night.

FamilyKitchenCheck-in

5.0 out of 5 average rating, 326 reviews
Guest favourite
A spacious living area features a light-colored sectional sofa facing a mounted TV above a decorative fireplace. The open-plan design connects to a modern kitchen with bar seating. Natural light enters through large windows adorned with light curtains, creating a relaxed atmosphere.
Apartment in West Loop

Spacious Downtown 3BR with Free Parking

A beautiful, modern, three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'll have the whole space to yourself with easy access to some of the best restaurants in the city, a free parking space on premise, and nearby access to public transportation to quickly get around the city. The interior is recently renovated with new furnishings, and provides a beautiful space to relax and recharge between outings.

FamilyIndoor spacesLaundry

4.92 out of 5 average rating, 171 reviews
Guest favourite
An ivy-covered brick facade presents a charming entrance. A black door with decorative window details is centered, flanked by a small garden featuring well-maintained greenery. A gravel pathway leads to the entrance, showcasing the unique character of the historic coach house.
Home in West Loop

Pro Cleaned & Isolated West Loop Coach House

Mimi & Paul's historic ivy-covered two-level coach house has a private entrance and an airy queen bedroom. The renovated kitchen is outfitted with European-sized appliances, though you'll probably have no time to cook since you're surrounded by the best restaurants Chicago has to offer. All of the essentials are provided to make your stay easy and products, soaps, shampoo/conditioner/body wash, towels, linens and even coffee/tea!

KitchenIndoor spacesOutdoor spaces

4.87 out of 5 average rating, 509 reviews
Superhost
Apartment in West Loop

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

KitchenIndoor spacesSleep quality

4.84 out of 5 average rating, 200 reviews
Top guest favourite
An open concept family room features a spacious sectional couch complemented by a small side table. A dining area with a table and blue chairs is present. Large windows allow natural light into the space, while exposed brick walls add character.
Apartment in West Loop

Gorgeous West Loop 3 Bedroom Loft

This beautiful 3 bedroom is located in the best location in Fulton Market. You are walking distance to every restaurant, shop and bar in the West Loop and the “L” is steps from the entrance which offers public transportation to the entire city. Our 3 bedroom, 2 bath sleeps 7 and is the perfect location for a family vacation or a group of friends looking to enjoy a fun weekend in one of the great cities on earth.

FamilyIndoor spacesHospitality

4.99 out of 5 average rating, 100 reviews
Superhost
A spacious studio apartment is showcased, featuring light-colored walls and hardwood flooring. Two ceiling fans provide airflow, while a comfortable bed is positioned adjacent to a cozy leather couch. A wooden dining table accommodates several chairs, and framed artwork adorns the walls.
Loft in West Town

OHC Gorgeous Huge Studio Apt Steps to Blue Line

Welcome to OHC Studio! Part of the Open House Contemporary family of art gallery airbnbs, this huge 1000 sq ft studio apartment is the perfect place to call home base while you explore Chicago. Featured in Architectural Digest (Aug. 2018) and as one of Bobby Berk's (Queer Eye's designer extraordinaire) top 10 Airbnbs in Condé Nast Traveler (Sept. 2018).

FamilyKitchenCleanliness

4.89 out of 5 average rating, 410 reviews

Popular amenities for West Loop family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Superhost
A bright and spacious living area features large panoramic windows that offer stunning skyline views. Stylish furniture is arranged around a modern dining table, complemented by a cozy seating area with a sofa and accent chairs. Decorative lighting hangs above, enhancing the contemporary design.
Apartment in West Loop

West Loop 2BR with Skyline Views + Prime Location

Indoor spacesFamilyCheck-in

4.82 out of 5 average rating, 109 reviews
Superhost
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Little Italy

Private hot tub - King bed suite - Free parking

FamilyIndoor spacesBackyard

4.92 out of 5 average rating, 283 reviews
Guest favourite
Condo in West Town

Chicago Oasis | Spa Bath, Patio & Fireplace

KitchenFamilyGetting around

4.96 out of 5 average rating, 183 reviews
Top guest favourite
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.
Condo in Ukrainian Village

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

FamilyKitchenAmenities

4.98 out of 5 average rating, 128 reviews
Guest favourite
The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.
Guesthouse in Chicago

Private Coach house near Lincoln Square!

KitchenFamilyLong stay

4.88 out of 5 average rating, 398 reviews
Top guest favourite
A modern kitchen features a large stainless steel island with seating for three. Black cabinetry offers ample storage space, complemented by open shelves displaying various kitchen items. Pendant lights hang above, illuminating a stylish workspace adorned with greenery, while industrial elements add character.
Loft in Wicker Park

Tea Studio in Wicker Park Spring Factory

FamilyKitchenOutdoor spaces

4.96 out of 5 average rating, 309 reviews
Guest favourite
A spacious living room features comfortable seating on soft gray furniture, including a large chaise and armchairs. Natural light brightens the area, while a gas fireplace is set within a stylish stone surround. A large flat-screen TV is mounted above the fireplace.
Home in Lake View

Entire house in Lakeview with yard and garage

FamilyKitchenHospitality

4.86 out of 5 average rating, 111 reviews
Top guest favourite
An elegantly furnished dining area features a wooden table with a textured runner. Dark leather chairs surround the table, and a modern chandelier hangs above. The open kitchen, equipped with stainless steel appliances and bar seating, is visible in the background.
Condo in Logan Square

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Indoor spacesKitchenNearby

4.98 out of 5 average rating, 329 reviews

Family- and pet-friendly home rentals

Guest favourite
A living area features exposed brick walls and polished hardwood floors. A comfortable sofa along with two wooden side tables, each topped with a lamp, is positioned for relaxing. Large windows allow natural light to fill the space, providing views of the outdoors.
Guest suite in West Town

The Huron Haven

Indoor spacesKitchenSleep quality

4.87 out of 5 average rating, 233 reviews
Superhost
An open living area displays a modern kitchen with stainless steel appliances and dark cabinetry. A light-colored sofa is positioned beside a wooden coffee table. A glass dining table accommodates four chairs, while a colorful rug adds warmth to the space.
Apartment in West Town

Explore the City from an Elegant, Urban Retreat

KitchenFamilyWalkability

4.85 out of 5 average rating, 456 reviews
Guest favourite
Apartment in West Loop

Beautiful Luxury Loft in Fulton Market, Sleeps 12

Indoor spacesKitchenSolo travel

4.85 out of 5 average rating, 281 reviews
Superhost
A contemporary living room features a large sectional sofa and a dark coffee table. A decorative wall art piece of a city skyline is displayed above the couch. The space includes a dining area with a round table and chairs, illuminated by overhead lighting.
Apartment in West Town

Unwind in the Garden of an elegant, Modern Home

FamilyIndoor spacesAccess

4.85 out of 5 average rating, 405 reviews
Superhost
A bright and open living space showcases a contemporary seating area with a green sofa and a plush armchair. Natural light floods through large windows, casting a warm glow over the stylish kitchenette and dining table. A smart TV is mounted on the wall, enhancing the modern vibe.
Apartment in Little Italy

Modern 1BR in Little Italy, Near West Loop

Indoor spacesFamilyHeating

4.9 out of 5 average rating, 176 reviews
Guest favourite
A spacious living area features large windows allowing abundant natural light. Exposed Chicago brick adds character to the space, while hardwood floors extend throughout. A comfortable sectional sofa, a chic armchair, and a tasteful area rug create a welcoming atmosphere. A television and decorative furnishings are also visible.
Apartment in West Town

✨Spacious Centrally Located West Loop Loft✨

FamilyKitchenSleep quality

4.91 out of 5 average rating, 331 reviews
Guest favourite
A spacious kitchen features modern cabinetry and stainless steel appliances. An island with bar seating for eight is complemented by sleek blue chairs. Natural light fills the area from large windows, illuminating the open layout that transitions into a cozy dining space.
Home in South Loop

Large Home | Free Parking | Near Downtown

KitchenFamilyDecor

4.89 out of 5 average rating, 129 reviews
Top guest favourite
Condo in Wicker Park

Two Bedroom w Porch in Wicker Park

FamilyKitchenParking

4.96 out of 5 average rating, 123 reviews

Family-friendly home rentals with a pool

Guest favourite
A spacious bedroom features large floor-to-ceiling windows, allowing natural light to fill the room. A large bed with neutral bedding is complemented by a contemporary desk and chair setup, which is arranged near a wood-framed lamp. A subtle area rug lies beneath the bed.
Apartment in Downtown Chicago

50th Floor Mag Mile Views, Balcony, Pool, Gym

Indoor spacesKitchenHospitality

4.9 out of 5 average rating, 143 reviews
Guest favourite
The modern kitchen features white cabinetry and a spacious island with four bar stools. A stainless steel refrigerator stands next to a gas stove and microwave. Natural light filters through large windows, illuminating the elegant countertops and sleek finishes.
Apartment in West Town

Cozy Duplex Down in Wicker Park East w/ Parking

Indoor spacesFamilyCheckout

4.93 out of 5 average rating, 131 reviews
Guest favourite
A large outdoor pool is surrounded by a modern deck featuring lounge chairs. High-rise buildings provide a city backdrop against a clear blue sky.
Apartment in Downtown Chicago

Highrise Hideout (Fitness Center • Sauna)

KitchenIndoor spacesWalkability

4.91 out of 5 average rating, 123 reviews
Top guest favourite
An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.
Apartment in Logan Square

Fun & cozy getaway w/POOL/game room/FREE parking

FamilyKitchenQuiet

4.98 out of 5 average rating, 172 reviews
Top guest favourite
An open-concept living area features large windows that invite natural light and provide a view of the cityscape. A comfortable blue sofa is adorned with patterned pillows, while a light wood coffee table sits in front of it. A dining space with black chairs complements the modern kitchen.
Condo in Evanston

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

KitchenIndoor spacesEV charging

4.96 out of 5 average rating, 142 reviews
Guest favourite
Apartment in The Loop

South Loop | Rooftop With In & Out Parking | 3

FamilyIndoor spacesHospitality

4.78 out of 5 average rating, 101 reviews
Guest favourite
A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.
Apartment in Uptown

Whole Flat in Private Club. Walk to L, Dining & Shows

KitchenFamilyHospitality

4.9 out of 5 average rating, 600 reviews
Guest favourite
Apartment in West Loop

West Loop Loft|Sleeps 4, Parking, Pool, & Rooftops

CheckoutAmenitiesCleanliness

5.0 out of 5 average rating, 6 reviews

Destinations to explore