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, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Jan 7 – 14
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov 18 – 25
Apartment in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Sep 4 – 11
Condo in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Apr 5 – 12
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Aug 6 – 13
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
Condo in Bronzeville
4.46 out of 5 average rating, 79 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Sep 27 – Oct 4
Family- and pet-friendly home rentals
Apartment in Chicago
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct 17 – 24
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec 3 – 10
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Mar 3 – 10
Apartment in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
Feb 14 – 21
Apartment in Irving Park
4.86 out of 5 average rating, 325 reviewsThe Avondale Garden Unit
Jul 1 – 8
Guest suite in Wood Dale
4.9 out of 5 average rating, 430 reviewsThe Deer Suite
Nov 1 – 8
Apartment in Forest Park
4.92 out of 5 average rating, 112 reviewsVillage Cottage - Forest Park Studio Pets 72142F
May 9 – 16
Apartment in Chicago
4.87 out of 5 average rating, 304 reviewsUnwind in the Garden of an elegant, Modern Home
Dec 4 – 11
Family-friendly home rentals with a pool
Apartment in Chicago
4.76 out of 5 average rating, 204 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Nov 17 – 24
Apartment in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Feb 5 – 12
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Mar 20 – 27
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Nov 11 – 18
Apartment in The Loop
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Oct 30 – Nov 6
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar 25 – Apr 1
Place to stay in Berwyn
Beat-Town Flex Stays
May 23 – 30
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