Kid-friendly holiday rentals in Downtown Chicago
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Downtown Chicago
Guests agree: these family-friendly rentals 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
Kid-friendly house rentals
Home in Chicago
Cozy & Modern Chic Full House in Trendy Bridgeport
Home in Chicago
Cozy garden apartment historic Jackson Bvld.
Home in Berwyn
Private apartment with retro vibe
Home in Chicago
Paradise on the Park
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
Home in Chicago
Private 3rd Floor Apartment
Home in Chicago
Wrigleyville Southport Studio
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
Family-friendly apartment rentals
Rental unit in Chicago
LAKESIDE PIED `A TERRE STEPS TO BEACH
Rental unit in Chicago
Designer Avondale Attic
Rental unit in Chicago
Ukrainian Village Garden Retreat
Rental unit in Chicago
Cute, Clean, Cozy Apartment in Pilsen
Rental unit in Chicago
La Cottage
Rental unit in Chicago
⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Rental unit in Chicago
Spacious & private! Free parking! Great location!
Rental unit in Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
Family-friendly apartment rentals
Apartment in Chicago
Quiet, Modern, Convenient 2 bedroom condo
Apartment in Chicago
3D Tour! Designer Condo near Logan Square
Apartment in Chicago
Stylish 3BR + Free Parking 10-15mins from Downtown
Apartment in Chicago
Private hot tub - King bed suite - Free parking
Apartment in Chicago
Near McCormick Place and Minutes from Downtown!
Apartment in Chicago
Urban Comfort in the Heart of Chicago
Apartment in Chicago
Unique Lincoln Park Duplex Apt
Apartment in Chicago
Updated Designer Duplex In Fulton Market W/parking
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
- Waterfront rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Beachfront rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Townhouse rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Monthly Rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Hotel rentals Downtown Chicago
- House rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Family-friendly rentals Milwaukee
- 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