Family-friendly holiday rentals in South Loop, Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in South Loop, Chicago
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 South Loop, Chicago family-friendly rentals
Family-friendly home rentals with a hot tub
Condo in Logan Square
Urban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in West Town
Lux Urban 3BR/3BA Duplex + Parking!
Rental unit in The Loop
The Professional's Playground
Condo in Irving Park
Chicago Suite 1BR/1BA (3709-G2)
Loft in West Town
Artist Loft Duplex in a 1904 Former Factory
Rental unit in Bronzeville
Spacious 2bdm unit 15min to Dwtn
Rental unit in The Loop
The Playwright's Palace
Rental unit in Chicago
Lux Loop Retreat: Amazing Views, Free Parking
Family- and pet-friendly home rentals
Rental unit in Logan Square
Relaxed Bucktown/Wicker Park 1B Apt
Rental unit in Logan Square
Sunny Logan Square Artists' home
Rental unit in Lincoln Park
Chicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Home in Uptown
Private 3rd Floor Apartment
Rental unit in West Town
Unwind in the Garden of an elegant, Modern Home
Condo in Chinatown
Charming Chinatown Home by McCormick★Downtown
Rental unit in Irving Park
The Avondale Garden Unit
Condo in Evanston
Spacious Evanston Unit - Walk to Northwestern U
Family-friendly home rentals with a pool
Rental unit in The Loop
Stylish Corner 2 Bedroom in the Heart of Chicago |
Guest suite in Berwyn
Music Hot Spot’s Main Level
Guest suite in Bridgeport
Sweet Home Chicago-9min downtown/pool/free parking
Rental unit in The Loop
Luxury Corner 2 Bedroom in the Loop | Roof Deck
Rental unit in The Loop
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Place to stay in Berwyn
Beat-Town Flex Stays
Quick stats about holiday rentals that are family-friendly in South Loop, Chicago
Total rentals
240 properties
Rentals with dedicated workspaces
190 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
50 properties allow pets
Total number of reviews
9.2K reviews
Nightly prices starting at
$129 NZD before taxes and fees
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Family-friendly rentals Illinois
- Rentals with a patio South Loop
- Apartment rentals South Loop
- Monthly Rentals South Loop
- Fitness-friendly rentals South Loop
- Rentals with outdoor seating South Loop
- Rentals with a fireplace South Loop
- Rentals with lake access South Loop
- Rentals with a washing machine and dryer South Loop
- Rentals with an EV charger South Loop
- Pet-friendly rentals South Loop
- Rentals with a hot tub South Loop
- Condo rentals South Loop
- Smoking-friendly rentals South Loop
- Rentals with a fire pit South Loop
- Family-friendly rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom