Family-friendly holiday rentals in Old Town, Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Old Town, 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 Old Town, Chicago family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Chicago
4.98 out of 5 average rating, 236 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Flat in Near South Side
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Home in West Town
4.85 out of 5 average rating, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
Flat in The Loop
4.81 out of 5 average rating, 27 reviewsThe Professional's Playground
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, 79 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Family- and pet-friendly home rentals
Flat in Chicago
4.83 out of 5 average rating, 482 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Flat in Chicago
4.74 out of 5 average rating, 191 reviewsCozy Bedroom in Wrigleyville (Entire Apt)
Apartment in Lincoln Park
4.83 out of 5 average rating, 311 reviewsChic and Charming Vintage Condominium in Lincoln Park
Flat in Logan Square
4.9 out of 5 average rating, 345 reviewsSunny Logan Square Artists' home
Home in Uptown
4.9 out of 5 average rating, 337 reviewsPrivate 3rd Floor Apartment
Apartment in Evanston
4.77 out of 5 average rating, 570 reviewsSpacious Evanston Unit - Walk to Northwestern U
Flat in Irving Park
4.86 out of 5 average rating, 327 reviewsThe Avondale Garden Unit
Flat in Chicago
4.87 out of 5 average rating, 305 reviewsUnwind in the Garden of an elegant, Modern Home
Family-friendly home rentals with a pool
Flat in The Loop
4.78 out of 5 average rating, 189 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
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, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Flat in The Loop
4.62 out of 5 average rating, 50 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Place to stay in Berwyn
Beat-Town Flex Stays
Quick stats about holiday rentals that are family-friendly in Old Town, Chicago
Total rentals
50 properties
Wifi availability
50 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
4K reviews
Nightly prices starting at
€ 65 before taxes and fees
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