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, 232 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
4–11 Jan
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
31 Aug – 7 Sep
Flat in Chicago
4.86 out of 5 average rating, 155 reviewsStunning Panoramic Chicago Views & Free Parking
2–9 Nov
Flat in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
2–9 Jan
Apartment in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
31 Mar – 7 Apr
Flat in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
5–12 Jul
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
4–11 Sep
Flat in Chicago
New place to stayThe Playwright's Palace
29 Nov – 6 Dec
Family- and pet-friendly home rentals
Apartment in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
27 Oct – 3 Nov
Flat in Chicago
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
9–16 Feb
Flat in Chicago
4.74 out of 5 average rating, 187 reviewsCozy Bedroom in Wrigleyville (Entire Apt)
7–14 Apr
Flat in Chicago
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
4–11 Apr
Flat in Chicago
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
14–21 Oct
Flat in Chicago
4.76 out of 5 average rating, 296 reviewsITALIAN garden apt/kids friendly/great location!!
25 Feb – 4 Mar
Guest suite in Wood Dale
4.9 out of 5 average rating, 427 reviewsThe Deer Suite
17–24 Oct
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
20–27 Jun
Family-friendly home rentals with a pool
Flat in Chicago
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
Flat in Forest Park
4.91 out of 5 average rating, 11 reviewsComfy & Cute-Oak Park Area - Parking +Public Trans
1–8 Sep
Flat 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
1–8 Feb
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
12–19 Dec
Flat in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
11–18 Sep
Flat 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 holiday rentals that are family-friendly in Chicago
Total rentals
4.8T properties
Wifi availability
4.7T properties include access to wifi
Rentals with dedicated workspaces
3.2T properties have a dedicated workspace
Rentals with a pool
300 properties have a pool
Pet-friendly rentals
1.7T properties allow pets
Total number of reviews
2.3L 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
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