Family-friendly vacation 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.
Vacation 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 Chicago
New place to stayLux Loop Retreat: Amazing Views, Free Parking
Family- and pet-friendly home rentals
Condo in Evanston
4.77 out of 5 average rating, 572 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
4.89 out of 5 average rating, 348 reviewsSunny Logan Square Artists' home
Apartment in Logan Square
4.83 out of 5 average rating, 484 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 298 reviewsa SIMPLE place
Apartment in Irving Park
4.86 out of 5 average rating, 329 reviewsThe Avondale Garden Unit
Apartment in Chicago
4.76 out of 5 average rating, 302 reviewsITALIAN garden apt/kids friendly/great location!!
Apartment in Lincoln Park
4.89 out of 5 average rating, 149 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
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 vacation rentals that are family-friendly in Chicago
Total rentals
4.8K properties
Wifi availability
4.7K properties include access to wifi
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
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