
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

Unbeatable Penthouse: Views, Central, Modern

Modern Wrigley Oasis with Parking!

Private Coach house near Lincoln Square!

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Lux Urban 3BR/3BA Duplex + Parking!

Tea Studio in Wicker Park Spring Factory

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

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

Flat in Lincoln Park 2-Flat Central to Everything

Lincoln Square Gem!

Logan Square Cozy 2BR Basement Apartment

Spectacular Penthouse Corner 2BR in Streeterville

Insta Worthy Prime Spot *Patio *Parking *Fireplace

Susie's Space. 2BR easy parking & pet friendly

Large Remodeled Home in Lincoln Park, Sleeps 12!

Elegant Suite in Gold Coast
Family-friendly home rentals with a pool

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool

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

Skyline Oasis: City & Lake Views

Level One Bedroom Suite | Fulton Market

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

Level ◆ New Luxe Two Bedroom Corner Suite

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

14th Floor 3Bd 3Bth Unit w/ Gym, Pool, &Amenities
Quick stats about vacation rentals that are family-friendly in Old Town
Total rentals
50 properties
Nightly prices starting at
€ 59 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
- Pet-friendly rentals Old Town
- Apartment rentals Old Town
- Rentals with a fireplace Old Town
- Rentals with a washer and dryer Old Town
- House rentals Old Town
- Rentals with a patio Old Town
- Rentals with outdoor seating 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
- Museum of Science and Industry
- Washington Park Zoo
- Lincoln Park Zoo
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The Beverly Country Club
- The 606