Family-friendly holiday rentals in Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chicago
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago family-friendly rentals
Family-friendly home rentals with a hot tub
Home in West Town
Lux Urban 3BR/3BA Duplex + Parking!
Apartment in Logan Square
Urban Luxury 1BR/2BA Logan Square Condo w/Garage
Rental unit in Chicago
Skyline Serenity: Sauna, Hot Tub, Peloton, Views
Rental unit in The Loop
The Professional's Playground
Apartment in Irving Park
Chicago Suite 1BR/1BA (3709-G2)
Rental unit in Bronzeville
Spacious 2bdm unit 15min to Dwtn
Loft in West Town
Artist Loft Duplex in a 1904 Former Factory
Rental unit in The Loop
The Playwright's Palace
Family- and pet-friendly home rentals
Apartment in Evanston
Spacious Evanston Unit - Walk to Northwestern U
Rental unit in Logan Square
Relaxed Bucktown/Wicker Park 1B Apt
Rental unit in Irving Park
The Avondale Garden Unit
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
Townhouse in Hoffman Estates
a SIMPLE place
Rental unit in Chicago
Urban Pilsen Apt. near Downtown
Rental unit in Lincoln Park
Chicago Lincoln Park Getaway
Rental unit in Irving Park
ITALIAN garden apt/kids friendly/great location!!
Family-friendly home rentals with a pool
Rental unit in The Loop
Luxury Corner 2 Bedroom in the Loop | Roof Deck
Guest suite in Berwyn
Music Hot Spot’s Main Level
Guest suite in Bridgeport
Sweet Home Chicago-9min downtown/pool/free parking
Rental unit in The Loop
Stylish Corner 2 Bedroom in the Heart of Chicago |
Rental unit in The Loop
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Place to stay in Berwyn
Beat-Town Flex Stays
Quick stats about holiday rentals that are family-friendly in Chicago
Total rentals
4.8T properties
Wifi availability
4.7T properties include access to wifi
Rentals with dedicated workspaces
3.2T properties have a dedicated workspace
Rentals with a pool
300 properties have a pool
Pet-friendly rentals
1.7T properties allow pets
Total number of reviews
2.3L reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Family-friendly rentals United States
- Beachfront rentals Chicago
- Smoking-friendly rentals Chicago
- Rentals with beach access Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with a fireplace Chicago
- Boutique hotel rentals Chicago
- Mansion rentals Chicago
- Lakehouse rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with a patio Chicago
- Private suite rentals Chicago
- Family-friendly rentals Chicago
- Bed and breakfasts Chicago
- Townhouse rentals Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Fitness-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with a washing machine and dryer Chicago
- Flat rentals Chicago
- Rentals with an EV charger Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- House rentals Chicago
- Rentals with a sauna Chicago
- Rentals with lake access Chicago
- Loft rentals Chicago
- Rentals with an accessible-height bed Chicago
- Monthly Rentals Chicago
- Waterfront rentals Chicago
- Rentals with a balcony Chicago
- Family-friendly rentals Downtown Chicago
- Family-friendly rentals Lake Geneva
- Family-friendly rentals Illinois
- Family-friendly rentals Cook County
- Yurt Rentals United States
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- Houseboats United States
- Holiday Caravans United Kingdom
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- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
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- Holiday Chalets United Kingdom
- Cottage Rentals United States
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- Villa Rentals United Kingdom
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- Condo Rentals United States
- Holiday Apartments Australia
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- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
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- Pet-Friendly Vacation Rentals United States
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- Luxury Dog-Friendly Cottages United Kingdom