Family-friendly vacation rentals in Downtown Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Downtown Chicago
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Downtown Chicago family-friendly rentals
Family-friendly home rentals with a hot tub
Condo in Chicago
4.98 out of 5 average rating, 235 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apartment in Near South Side
4.87 out of 5 average rating, 159 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in The Loop
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Apartment 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 The Loop
5.0 out of 5 average rating, 4 reviewsThe Playwright's Palace
Family- and pet-friendly home rentals
Apartment in Irving Park
4.86 out of 5 average rating, 326 reviewsThe Avondale Garden Unit
Apartment in Logan Square
4.83 out of 5 average rating, 482 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Irving Park
4.76 out of 5 average rating, 300 reviewsITALIAN garden apt/kids friendly/great location!!
Apartment in West Loop
4.93 out of 5 average rating, 214 reviews✨Spacious Centrally Located West Loop Loft✨
Guest suite in Wood Dale
4.9 out of 5 average rating, 431 reviewsThe Deer Suite
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Apartment in Chicago
4.87 out of 5 average rating, 304 reviewsUnwind in the Garden of an elegant, Modern Home
Family-friendly home rentals with a pool
Apartment in Chicago
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
Apartment in Chicago
4.77 out of 5 average rating, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Apartment 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
Destinations to explore
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