Kid-friendly holiday rentals in Chicago
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Chicago
Guests agree: these family-friendly rentals 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
Kid-friendly house rentals
Home in West Loop
Cozy garden apartment historic Jackson Bvld.
Home in Berwyn
Private apartment with retro vibe
Home in Pilsen Historic District
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
Home in Bridgeport
Cozy & Modern Chic Full House in Trendy Bridgeport
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
Home in Joliet
Cozy Private Cottage in the Cathedral District
Home in Uptown
Private 3rd Floor Apartment
Home in West Town
Paradise on the Park
Family-friendly apartment rentals
Rental unit in Logan Square
Bright & Lofty Bucktown 1br
Rental unit in West Town
Fully Furnished Apartment Wicker Park Free Parking
Rental unit in Lincoln Park
Redesigned Lower Level Studio in Historic Building
Rental unit in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
Rental unit in Uptown
Cozy loft in Chicago's Uptown
Rental unit in Andersonville
Sunny, Cozy, Colorful Andersonville
Rental unit in Andersonville
Lovely Andersonville Apt with Ideal Location
Rental unit in Skokie
Cozy Garden Unit in Quiet Neighborhood
Family-friendly apartment rentals
Apartment in Jefferson Park
-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
Apartment in Little Italy
Private hot tub - King bed suite - Free parking
Apartment in Chicago
Near McCormick Place and Minutes from Downtown!
Apartment in Lake View
Urban Comfort in the Heart of Chicago
Apartment in Lincoln Park
Unique Lincoln Park Duplex Apt
Apartment in Humboldt Park
3D Tour! Designer Condo near Logan Square
Apartment in Andersonville
The Bright Retreat in Andersonville
Apartment in West Town
Spacious Duplex in Great Location
Quick stats about holiday rentals that are kid-friendly in Chicago
Total rentals
1.3K properties
Rentals with dedicated workspaces
1K properties have a dedicated workspace
Rentals with a pool
110 properties have a pool
Pet-friendly rentals
580 properties allow pets
Family-friendly rentals
980 properties are a good fit for families
Total number of reviews
78K 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
- Flat rentals Chicago
- Rentals with a patio Chicago
- Rentals with beach access Chicago
- Fitness-friendly rentals Chicago
- Guest house rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with a sauna Chicago
- Lakehouse rentals Chicago
- Rentals with a fireplace Chicago
- Family-friendly rentals Chicago
- Bed and breakfasts Chicago
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- Rentals with a firepit Chicago
- Mansion rentals Chicago
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- Rentals with an EV charger Chicago
- Beachfront rentals Chicago
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- House rentals Chicago
- Private suite rentals Chicago
- Rentals with pools Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with an accessible-height bed Chicago
- Smoking-friendly rentals Chicago
- Hotel rentals Chicago
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- Monthly Rentals Chicago
- Boutique hotel rentals Chicago
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- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Family-friendly rentals Downtown Chicago
- Family-friendly rentals Milwaukee
- Family-friendly rentals Lake Geneva
- Family-friendly rentals Illinois
- Family-friendly rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- 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
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows 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
- Beach Condos United States
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- Beach Houses United Kingdom
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- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom