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
Apartment in Chicago
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in West Town
4.85 out of 5 average rating, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
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
Apartment in Chicago
4.46 out of 5 average rating, 80 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Family- and pet-friendly home rentals
Apartment in Evanston
4.77 out of 5 average rating, 570 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
Flat in Logan Square
4.89 out of 5 average rating, 347 reviewsSunny Logan Square Artists' home
Flat in Irving Park
4.86 out of 5 average rating, 328 reviewsThe Avondale Garden Unit
Flat in Wicker Park
4.83 out of 5 average rating, 483 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Flat in Chicago
4.75 out of 5 average rating, 191 reviewsCozy Bedroom in Wrigleyville (Entire Apt)
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Flat in Chicago
4.83 out of 5 average rating, 131 reviewsChicago Lincoln Park Getaway
Family-friendly home rentals with a pool
Flat in The Loop
4.77 out of 5 average rating, 191 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Flat in Chicago
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in The Loop
4.83 out of 5 average rating, 29 reviewsThe Professional's Playground
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, 206 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Flat in Chicago
New place to stayLux Loop Retreat: Amazing Views, Free Parking
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
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Townhouse rentals Chicago
- Bed and breakfasts Chicago
- Rentals with a washing machine and dryer Chicago
- Family-friendly rentals Chicago
- Lakehouse rentals Chicago
- Loft rentals Chicago
- Rentals with lake access Chicago
- Rentals with an accessible-height toilet Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- House rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Private suite rentals Chicago
- Flat rentals Chicago
- Guest house rentals Chicago
- Rentals with an EV charger Chicago
- Smoking-friendly rentals Chicago
- Mansion rentals Chicago
- Beachfront rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with an accessible-height bed Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Monthly Rentals Chicago
- Rentals with a patio Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with a sauna Chicago
- Waterfront rentals Chicago
- Fitness-friendly 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
- 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
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- 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
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom