Family-friendly holiday houses 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
Condo in Logan Square
4.98 out of 5 average rating, 232 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
5 – 12 Jan
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
31 Aug – 7 Sept
Apartment in Chicago
4.86 out of 5 average rating, 155 reviewsStunning Panoramic Chicago Views & Free Parking
4 – 11 Oct
Apartment in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
2 – 9 Jan
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
2 – 9 Nov
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
5 – 12 July
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
5 – 12 Sept
Apartment in The Loop
New place to stayThe Playwright's Palace
27 June – 4 July
Family- and pet-friendly home rentals
Condo in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
2 – 9 Dec
Apartment in Chicago
4.74 out of 5 average rating, 187 reviewsCozy Bedroom in Wrigleyville (Entire Apt)
18 – 25 Dec
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
1 – 8 Dec
Apartment in Chicago
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
4 – 11 Apr
Apartment in Chicago
4.76 out of 5 average rating, 297 reviewsITALIAN garden apt/kids friendly/great location!!
11 – 18 Dec
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
20 – 27 June
Apartment in Chicago
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
5 – 12 Oct
Guest suite in Wood Dale
4.9 out of 5 average rating, 427 reviewsThe Deer Suite
17 – 24 Oct
Family-friendly home rentals with a pool
Apartment in The Loop
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
8 – 15 Feb
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
12 – 19 Jan
Apartment in Forest Park
4.91 out of 5 average rating, 11 reviewsComfy & Cute-Oak Park Area - Parking +Public Trans
1 – 8 Sept
Apartment in Chicago
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
12 – 19 Feb
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
17 – 24 Apr
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
15 – 22 Dec
Apartment in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
11 – 18 Sept
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
24 – 31 Mar
Quick stats about accommodation & holiday rentals that are family-friendly in Chicago
Total rentals
4.8K properties
Wi-Fi availability
4.7K properties include access to Wi-Fi
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
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