
Family-friendly holiday rentals in Chicago Loop
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chicago Loop
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago Loop family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Wrigley Oasis with Parking!

Private Coach house near Lincoln Square!

Lux Urban 3BR/3BA Duplex + Parking!

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

Tea Studio in Wicker Park Spring Factory

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

Belmont Pleasures - hot tub / arcade gaming room

Checkerboard Studio, Private Outdoor Hot Tub, Yard
Family- and pet-friendly home rentals

Chicago Living: Your Home Away From Home

Stylish 2BR stunner w/ unbeatable location

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Retro Modern Bungalow | fire pit | free parking

Eddy Street Upstairs Apartment

Garden on Warren
Explore the City from an Elegant, Urban Retreat

Great location. Free parking.
Family-friendly home rentals with a pool

Level ◆ Brand New Luxe One Bedroom

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

Luxury Designer Penthouse NW | Pool | Gold Coast

Lux Skyhouse West Loop w/Parking

Skyline Oasis: City & Lake Views

Luxury Loft with Private Pool and Movie Theater

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

Million Dollar Views! Luxury Downtown Skyhouse!
Quick stats about holiday rentals that are family-friendly in Chicago Loop
Total rentals
300 properties
Nightly prices starting at
$120 NZD before taxes and fees
Total number of reviews
12K reviews
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
150 properties have a pool
Rentals with dedicated workspaces
210 properties have a dedicated workspace
Destinations to explore
- Serviced apartment rentals Chicago Loop
- Waterfront rentals Chicago Loop
- Rentals with breakfast Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with an EV charger Chicago Loop
- Apartment rentals Chicago Loop
- Condo rentals Chicago Loop
- Rentals with a home theatre Chicago Loop
- Loft rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with a patio Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with a hot tub Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Rentals with a washing machine and dryer Chicago Loop
- Rentals with beach access Chicago Loop
- 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
- Illinois Beach State Park
- Washington Park Zoo
- Garfield Park Conservatory
- Wicker Park
- Brookfield Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago Loop
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- Art and culture Chicago
- Sightseeing Chicago
- Food and drink Chicago
- Nature and outdoors Chicago
- Sports activities Chicago
- Things to do Cook County
- Sports activities Cook County
- Tours Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Things to do Illinois
- Nature and outdoors Illinois
- Food and drink Illinois
- Tours Illinois
- Sports activities Illinois
- Sightseeing Illinois
- Art and culture Illinois
- Things to do United States
- Tours United States
- Sightseeing United States
- Entertainment United States
- Sports activities United States
- Wellness United States
- Food and drink United States
- Art and culture United States
- Nature and outdoors United States