
Family-friendly vacation rentals in Old Town
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Old Town
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 family-friendly rentals
Family-friendly home rentals with a hot tub

Lux Urban 3BR/3BA Duplex + Parking!

Smart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities

Super Paradise *Downtown 15 Minutes *63 Amenities

Spacious 2bdm unit 15min to Dwtn

Bright and Beautiful Penthouse - Close to the lake

Restful Refuge, Hot Tub, Firepit, Dunes Nat’l Park

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

Urban Luxury 1BR/2BA Logan Square Condo w/Garage
Family- and pet-friendly home rentals

2 King Beds /Easy Downtown / Free Str Parking-Read

Private 3rd Floor Apartment

Stylish Studio in Historic Logan Square

Stunning Old Town Penthouse with Private Rooftop

Modern Logan Square Apartment near Public Transit

Insta Worthy Prime Spot *Patio *Parking *Fireplace

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Logan Square Video Game Loft
Family-friendly home rentals with a pool

Beautiful 137 Year Old Farm Home (3night min)

Stylish Corner 2 Bedroom in the Heart of Chicago |

Music Hot Spot’s Main Level

"A" Frame Brandenburg Lake

Beat-Town Flex Stays

Luxury Corner 2 Bedroom in the Loop | Roof Deck
Quick stats about vacation rentals that are family-friendly in Old Town
Total rentals
50 properties
Nightly prices starting at
$95 CAD before taxes and fees
Total number of reviews
4.7K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
Destinations to explore
- Rentals with a patio Old Town
- Rentals with a fireplace Old Town
- Kid-friendly rentals Old Town
- Apartment rentals Old Town
- Rentals with outdoor seating Old Town
- Rentals with a washer and dryer Old Town
- Pet-friendly rentals Old Town
- House rentals Old Town
- Family-friendly rentals Cook County
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Lincoln Park
- The Field Museum
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Garfield Park Conservatory
- Wicker Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- Chicago Cultural Center