
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

Modern Wrigley Oasis with Parking!

Private Coach house near Lincoln Square!

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Pet Fndly

Lux Urban 3BR/3BA Duplex + Parking!

Tea Studio in Wicker Park Spring Factory

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Penthouse Near Fulton: Skyline, Spacious

Belmont Pleasures - hot tub / arcade gaming room
Family- and pet-friendly home rentals

Sounds Of The City

Spectacular Penthouse Corner 2BR in Streeterville

Modern vintage chic steps from Wrigley Field!

Large Remodeled Home in Lincoln Park, Sleeps 12!

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Great location. Free parking.

Newly Renovated, Spacious 2BR in Andersonville

Newly Renovated 1BD near West Loop & Little Italy
Family-friendly home rentals with a pool

Level ◆ Brand New Luxe One Bedroom

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Skyline Oasis: City & Lake Views

Luxury Loft with Private Pool and Movie Theater

Whole Flat in Private Club. Walk to L, Dining & Shows

The Executive's Escape (2BD / 2BA)

Million Dollar Views! Luxury Downtown Skyhouse!

50th Floor Mag Mile Studio
Quick stats about vacation rentals that are family-friendly in Old Town
Total rentals
50 properties
Nightly prices starting at
G$14,639 GYD 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
- House rentals Old Town
- Rentals with outdoor seating Old Town
- Rentals with a fireplace Old Town
- Apartment rentals Old Town
- Rentals with a washer and dryer Old Town
- Pet-friendly rentals Old Town
- Rentals with a patio Old Town
- Family-friendly rentals Chicago
- Family-friendly rentals Cook County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Garfield Park Conservatory
- Illinois Beach State Park
- Wicker Park
- Lincoln Park Zoo
- Washington Park Zoo
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club