Family-friendly vacation rentals in Old Town, Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Old Town, 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 Old Town, 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
Jan 24 – 31
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov 10 – 17
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Apr 20 – 27
Apartment in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
Jan 2 – 9
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Oct 27 – Nov 3
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
Jul 25 – Aug 1
Condo in Bronzeville
4.45 out of 5 average rating, 78 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Sep 17 – 24
Family- and pet-friendly home rentals
Apartment in Wrigleyville
4.74 out of 5 average rating, 187 reviewsCozy Bedroom in Wrigleyville (Entire Apt)
Apr 13 – 20
Apartment in Lincoln Park
4.89 out of 5 average rating, 144 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Oct 1 – 8
Condo in West Town
4.88 out of 5 average rating, 234 reviews2 King Bed Condo Easy Downtown Free Street Parking
Mar 11 – 18
Condo in Lincoln Park
4.83 out of 5 average rating, 308 reviewsChic and Charming Vintage Condominium in Lincoln Park
Jan 29 – Feb 5
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Dec 1 – 8
Home in Avondale
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Dec 19 – 26
Apartment in Chicago
4.88 out of 5 average rating, 302 reviewsUnwind in the Garden of an elegant, Modern Home
Nov 26 – Dec 3
Apartment in Irving Park
4.76 out of 5 average rating, 298 reviewsITALIAN garden apt/kids friendly/great location!!
Nov 12 – 19
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 8 – 15
Apartment in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Jun 10 – 17
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Dec 9 – 16
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Dec 15 – 22
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 Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar 24 – 31
Place to stay in Berwyn
Beat-Town Flex Stays
Feb 25 – Mar 4
Quick stats about vacation rentals that are family-friendly in Old Town, Chicago
Total rentals
50 properties
Wifi availability
50 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
4K reviews
Nightly prices starting at
R1,317 ZAR before taxes and fees
Destinations to explore
- Family-friendly rentals United States
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