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, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in Chicago
4.85 out of 5 average rating, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apartment in Chicago
4.87 out of 5 average rating, 165 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in The Loop
4.83 out of 5 average rating, 30 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 Chicago
5.0 out of 5 average rating, 8 reviewsThe Playwright's Palace
Family- and pet-friendly home rentals
Apartment in Chicago
4.83 out of 5 average rating, 485 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Guest suite in Logan Square
4.97 out of 5 average rating, 243 reviewsStylish Studio in Historic Logan Square
Apartment in Lincoln Park
4.88 out of 5 average rating, 153 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Chicago
4.87 out of 5 average rating, 307 reviewsUnwind in the Garden of an elegant, Modern Home
Apartment in Irving Park
4.86 out of 5 average rating, 329 reviewsThe Avondale Garden Unit
Apartment in Chicago
4.76 out of 5 average rating, 302 reviewsITALIAN garden apt/kids friendly/great location!!
Home in Chicago
4.9 out of 5 average rating, 339 reviewsPrivate 3rd Floor Apartment
Family-friendly home rentals with a pool
Apartment in Chicago
4.77 out of 5 average rating, 207 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
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, 191 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Apartment in The Loop
4.6 out of 5 average rating, 52 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Place to stay in Berwyn
Beat-Town Flex Stays
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