Family-friendly holiday rentals in Downtown Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Downtown 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 Downtown Chicago family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Chicago
Urban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in Chicago
Lux Urban 3BR/3BA Duplex + Parking!
Rental unit in Chicago
Skyline Serenity: Sauna, Hot Tub, Peloton, Views
Rental unit in Chicago
The Professional's Playground
Apartment in Chicago
Chicago Suite 1BR/1BA (3709-G2)
Rental unit in Chicago
Spacious 2bdm unit 15min to Dwtn
Loft in Chicago
Artist Loft Duplex in a 1904 Former Factory
Rental unit in Chicago
The Playwright's Palace
Family- and pet-friendly home rentals
Rental unit in Chicago
Relaxed Bucktown/Wicker Park 1B Apt
Rental unit in Chicago
Urban Pilsen Apt. near Downtown
Rental unit in Chicago
The Avondale Garden Unit
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
Apartment in Evanston
Spacious Evanston Unit - Walk to Northwestern U
Rental unit in Chicago
Chicago Lincoln Park Getaway
Rental unit in Chicago
✨Spacious Centrally Located West Loop Loft✨
Rental unit in Chicago
ITALIAN garden apt/kids friendly/great location!!
Family-friendly home rentals with a pool
Rental unit in Chicago
Luxury Corner 2 Bedroom in the Loop | Roof Deck
Guest suite in Berwyn
Music Hot Spot’s Main Level
Guest suite in Chicago
Sweet Home Chicago-9min downtown/pool/free parking
Rental unit in Chicago
Stylish Corner 2 Bedroom in the Heart of Chicago |
Rental unit in Chicago
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Place to stay in Berwyn
Beat-Town Flex Stays
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Rentals with a patio Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- House rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Rentals with pools Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with lake access Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Waterfront rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Monthly Rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Family-friendly rentals Lake Geneva
- Family-friendly rentals Illinois
- 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