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, 238 reviewsPrivate apartment with retro vibe
14–21 Sep
Home in Chicago
4.94 out of 5 average rating, 209 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
1–8 Mar
Home in Chicago
4.96 out of 5 average rating, 316 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
4–11 Jan
Home in Chicago
4.95 out of 5 average rating, 171 reviewsParadise on the Park
15–22 Jan
Home in Lake View
4.98 out of 5 average rating, 205 reviewsWrigleyville Southport Studio
28 Nov – 5 Dec
Home in Chicago
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
5–10 Apr
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
5–12 Feb
Home in Whiting
4.8 out of 5 average rating, 225 reviewsWhiting Getaway
28 Oct – 4 Nov
Family-friendly apartment rentals
Flat in Lincoln Square
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
13–20 Sep
Flat in Chicago
4.99 out of 5 average rating, 229 reviewsA Whimsical Fairy-tale Loft in Ravenswood Chicago
24–31 Jan
Flat in Avondale
4.97 out of 5 average rating, 117 reviewsDesigner Avondale Attic
11–18 Jul
Flat in Chicago
4.98 out of 5 average rating, 297 reviewsRedesigned Lower Level Studio in Historic Building
3–10 Oct
Flat in Forest Park
5.0 out of 5 average rating, 219 reviewsLike a Treehouse!
2–9 Oct
Flat in Chicago
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
10–17 Nov
Flat in Cicero
4.98 out of 5 average rating, 201 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
11–18 Dec
Flat in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
4–11 Apr
Family-friendly apartment rentals
Apartment in Chicago
4.86 out of 5 average rating, 123 reviews3D Tour! Designer Condo near Logan Square
9–16 Jan
Apartment in Chicago
4.87 out of 5 average rating, 107 reviewsSpacious Duplex in Great Location
9–16 Jun
Apartment in Chicago
4.93 out of 5 average rating, 186 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
26 Jan – 2 Feb
Apartment in Chicago
4.91 out of 5 average rating, 120 reviewsSpacious & Modern Family Friendly North Center Apt
25 Jan – 1 Feb
Apartment in Oak Park
4.88 out of 5 average rating, 163 reviewsAttractive Flat - Historic Oak Park
29 Oct – 5 Nov
Apartment in West Town
4.86 out of 5 average rating, 435 reviewsHumboldt Park Traveler's Lodge
20–27 May
Apartment in West Town
4.86 out of 5 average rating, 191 reviewsBold Ukrainian Village 2 Bedroom w/Garage Parking
2–9 Jan
Apartment in Lincoln Park
4.95 out of 5 average rating, 439 reviewsUnique Lincoln Park Duplex Apt
26 Sep – 3 Oct
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
- Lakehouse rentals Chicago
- 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
- Family-friendly rentals Milwaukee
- Family-friendly rentals Chicago Loop
- 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
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom