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 Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apartment in Chicago
4.98 out of 5 average rating, 235 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Flat in Chicago
4.87 out of 5 average rating, 157 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Apartment in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Flat 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
Flat in The Loop
5.0 out of 5 average rating, 4 reviewsThe Playwright's Palace
Family- and pet-friendly home rentals
Apartment in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Flat in Logan Square
4.89 out of 5 average rating, 341 reviewsSunny Logan Square Artists' home
Flat in Irving Park
4.86 out of 5 average rating, 325 reviewsThe Avondale Garden Unit
Flat in Chicago
4.83 out of 5 average rating, 481 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Flat in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Guest suite in Portage Park
4.95 out of 5 average rating, 120 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
Home in Forest Park
4.91 out of 5 average rating, 224 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Family-friendly home rentals with a pool
Flat in Chicago
4.78 out of 5 average rating, 189 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Flat in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
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
Flat in Chicago
4.77 out of 5 average rating, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Flat in The Loop
4.61 out of 5 average rating, 49 reviewsStylish 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
4.8K 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
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
- Rentals with a balcony Chicago
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- Family-friendly rentals Downtown Chicago
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