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 Berwyn
4.92 out of 5 average rating, 237 reviewsPrivate apartment with retro vibe
7–14 Sept
Home in Avondale
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
26 Feb – 5 Mar
Home in Chicago
4.95 out of 5 average rating, 171 reviewsParadise on the Park
6–13 Nov
Home in Chicago
4.96 out of 5 average rating, 316 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
2–9 Dec
Home in Lake View
4.98 out of 5 average rating, 205 reviewsWrigleyville Southport Studio
29 Oct – 5 Nov
Home in Chicago
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
5–10 Dec
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
20–27 Jun
Home in Whiting
4.8 out of 5 average rating, 225 reviewsWhiting Getaway
11–18 Jan
Family-friendly apartment rentals
Flat in Chicago
4.88 out of 5 average rating, 104 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
27 Mar – 3 Apr
Flat in Lincoln Park
4.83 out of 5 average rating, 208 reviewsCozy Lincoln Park Studio - Steps to Zoo!
10–17 Jan
Flat in Lincoln Square
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
30 Sept – 7 Oct
Flat in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
13–20 Jul
Flat in Near North Side
4.89 out of 5 average rating, 370 reviewsGreat Location Studio in the Gold Coast!!
22–29 Jan
Flat in Chicago
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
13–20 Nov
Flat in Avondale
4.97 out of 5 average rating, 117 reviewsDesigner Avondale Attic
11–18 Jul
Flat in West Town
4.96 out of 5 average rating, 262 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
22–29 Dec
Family-friendly apartment rentals
Apartment in West Town
4.97 out of 5 average rating, 703 reviewsGreat location. Free parking.
Apartment in Oak Park
4.88 out of 5 average rating, 163 reviewsAttractive Flat - Historic Oak Park
2–9 May
Apartment in Chicago
4.92 out of 5 average rating, 110 reviewsStunning, Spacious, & Sun-Soaked 1br Uptown Condo
10–17 Jan
Apartment in East Rogers Park
4.93 out of 5 average rating, 186 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
9–16 Apr
Apartment in West Town
4.86 out of 5 average rating, 435 reviewsHumboldt Park Traveler's Lodge
20–27 May
Apartment in Lincoln Park
4.95 out of 5 average rating, 438 reviewsUnique Lincoln Park Duplex Apt
26 Sept – 3 Oct
Apartment in Chicago
4.98 out of 5 average rating, 232 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
4–11 Jan
Apartment in Chicago
4.87 out of 5 average rating, 107 reviewsSpacious Duplex in Great Location
16–23 Aug
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
- Rentals with a hot tub Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Apartment rentals Chicago
- Hotel rentals Chicago
- Rentals with a cinema Chicago
- Beachfront rentals Chicago
- Guest house rentals Chicago
- Private suite rentals Chicago
- Fitness-friendly rentals Chicago
- Loft rentals Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a sauna Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Monthly Rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a washing machine and dryer Chicago
- Family-friendly rentals Chicago
- Rentals with a firepit Chicago
- Rentals with outdoor seating Chicago
- Waterfront rentals Chicago
- Rentals with breakfast Chicago
- Mansion rentals Chicago
- Rentals with a patio Chicago
- Flat rentals Chicago
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- Boutique hotel rentals Chicago
- Townhouse rentals Chicago
- Villa rentals Chicago
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- Smoking-friendly rentals Chicago
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- Family-friendly rentals Downtown Chicago
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- 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
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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
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- Pet-Friendly Vacation Rentals United States
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- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom