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, 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
Home in McHenry
4.93 out of 5 average rating, 218 reviewsRiver House with Deck and Hot Tub
Jul 9 – 16
Home in Lake Villa
4.87 out of 5 average rating, 38 reviewsLakeside Getaway
Jul 24 – 31
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
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
Home in Miller Beach
4.54 out of 5 average rating, 150 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
May 18 – 25
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
Apartment in Chicago
4.74 out of 5 average rating, 187 reviewsCozy Bedroom in Wrigleyville (Entire Apt)
Feb 25 – Mar 4
Townhouse in Chicago
4.74 out of 5 average rating, 197 reviewsInsta Worthy Prime Spot *Patio *Parking *Fireplace
Jan 23 – 30
Apartment in Chicago
4.89 out of 5 average rating, 340 reviewsSunny Logan Square Artists' home
Jan 4 – 11
Apartment in Chicago
4.87 out of 5 average rating, 304 reviewsUnwind in the Garden of an elegant, Modern Home
Dec 4 – 11
Apartment in Chicago
4.86 out of 5 average rating, 325 reviewsThe Avondale Garden Unit
Jul 1 – 8
Apartment in Chicago
4.89 out of 5 average rating, 263 reviewsRiver North's Rock N Roll
Jan 8 – 15
Condo in Chicago
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Oct 30 – Nov 6
Family-friendly home rentals with a pool
Chalet in Ingleside
4.84 out of 5 average rating, 369 reviews"A" Frame Brandenburg Lake
Nov 16 – 23
Apartment in Chicago
4.76 out of 5 average rating, 204 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Nov 17 – 24
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Dec 31 – Jan 7
Apartment in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Sep 4 – 11
Apartment in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Jan 8 – 15
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Mar 20 – 27
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Nov 11 – 18
Apartment in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Oct 30 – Nov 6
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
G$14,605 GYD before taxes and fees
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- Family-friendly rentals United States
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