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, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Apr 29 – May 6
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov 12 – 19
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 1 – 8
Apartment in Chicago
4.8 out of 5 average rating, 25 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)
Apr 6 – 13
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
Oct 12 – 19
Apartment in The Loop
New place to stayThe Playwright's Palace
Jan 12 – 19
Family- and pet-friendly home rentals
Apartment in Irving Park
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Mar 3 – 10
Apartment in Irving Park
4.76 out of 5 average rating, 298 reviewsITALIAN garden apt/kids friendly/great location!!
Oct 25 – Nov 1
Apartment in Chicago
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct 15 – 22
Condo in West Town
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Sep 13 – 20
Condo in Evanston
4.76 out of 5 average rating, 567 reviewsSpacious Evanston Unit - Walk to Northwestern U
Feb 18 – 25
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Feb 10 – 17
Guest suite in Wood Dale
4.9 out of 5 average rating, 429 reviewsThe Deer Suite
Dec 13 – 20
Apartment in Chicago
4.88 out of 5 average rating, 302 reviewsUnwind in the Garden of an elegant, Modern Home
Feb 22 – Mar 1
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
Feb 12 – 19
Apartment in Chicago
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Jan 3 – 10
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Dec 6 – 13
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Nov 23 – 30
Apartment in The Loop
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Sep 11 – 18
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
Dec 24 – 31
Destinations to explore
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