Family-friendly holiday houses 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
4.85 out of 5 average rating, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
Condo in Chicago
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Apartment in Near South Side
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in Chicago
4.83 out of 5 average rating, 29 reviewsThe Professional's Playground
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Apartment in The Loop
5.0 out of 5 average rating, 5 reviewsThe Playwright's Palace
Family- and pet-friendly home rentals
Condo in Evanston
4.77 out of 5 average rating, 571 reviewsSpacious Evanston Unit - Walk to Northwestern U
Home in Forest Park
4.91 out of 5 average rating, 225 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Apartment in Logan Square
4.83 out of 5 average rating, 484 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Irving Park
4.86 out of 5 average rating, 329 reviewsThe Avondale Garden Unit
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 297 reviewsa SIMPLE place
Home in Uptown
4.9 out of 5 average rating, 338 reviewsPrivate 3rd Floor Apartment
Apartment in Chicago
4.97 out of 5 average rating, 458 reviewsFully Furnished Apartment Wicker Park Free Parking
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Family-friendly home rentals with a pool
Apartment in The Loop
4.77 out of 5 average rating, 191 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Apartment in Chicago
4.77 out of 5 average rating, 206 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Apartment in Chicago
4.62 out of 5 average rating, 50 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Place to stay in Berwyn
Beat-Town Flex Stays
Quick stats about accommodation & holiday rentals that are family-friendly in Chicago
Total rentals
4.8K properties
Wi-Fi availability
4.7K properties include access to Wi-Fi
Rentals with dedicated workspaces
3.2K properties have a dedicated workspace
Rentals with a pool
300 properties have a pool
Pet-friendly rentals
1.7K properties allow pets
Total number of reviews
233K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
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- New Buffalo Holiday rentals
- Family-friendly rentals United States
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