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
Mar 18 – 25
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov 14 – 21
Apartment in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Nov 17 – 24
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Mar 21 – 28
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Jun 13 – 20
Apartment in The Loop
5.0 out of 5 average rating, 3 reviewsThe Playwright's Palace
Dec 23 – 30
Condo in Chicago
4.46 out of 5 average rating, 79 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Sep 1 – 8
Family- and pet-friendly home rentals
Apartment in Wicker Park
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Sep 12 – 19
Apartment in Irving Park
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Jan 12 – 19
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec 2 – 9
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Feb 10 – 17
Home in Uptown
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Dec 18 – 25
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 294 reviewsa SIMPLE place
Feb 19 – 26
Apartment in Irving Park
4.76 out of 5 average rating, 298 reviewsITALIAN garden apt/kids friendly/great location!!
Feb 16 – 23
Apartment in River North
4.89 out of 5 average rating, 262 reviewsRiver North's Rock N Roll
Dec 31 – Jan 7
Family-friendly home rentals with a pool
Apartment in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Dec 14 – 21
Apartment in The Loop
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Apr 12 – 19
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Aug 8 – 15
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Dec 18 – 25
Apartment in The Loop
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Nov 26 – Dec 3
Apartment in The Loop
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar 11 – 18
Place to stay in Berwyn
Beat-Town Flex Stays
Mar 4 – 11
Destinations to explore
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