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
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in West Town
4.85 out of 5 average rating, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apartment in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Flat in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Apartment in Bronzeville
4.46 out of 5 average rating, 80 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Family- and pet-friendly home rentals
Flat in Irving Park
4.86 out of 5 average rating, 328 reviewsThe Avondale Garden Unit
Home in Forest Park
4.91 out of 5 average rating, 225 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Flat in Wicker Park
4.83 out of 5 average rating, 483 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Evanston
4.77 out of 5 average rating, 570 reviewsSpacious Evanston Unit - Walk to Northwestern U
Flat in Chicago
4.83 out of 5 average rating, 131 reviewsChicago Lincoln Park Getaway
Flat in Irving Park
4.76 out of 5 average rating, 302 reviewsITALIAN garden apt/kids friendly/great location!!
Apartment in Chinatown
4.94 out of 5 average rating, 178 reviewsCharming Chinatown Home by McCormick★Downtown
Family-friendly home rentals with a pool
Flat in The Loop
4.77 out of 5 average rating, 191 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Flat in Chicago
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in Chicago
4.83 out of 5 average rating, 29 reviewsThe Professional's Playground
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Flat in Chicago
4.77 out of 5 average rating, 206 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Flat in Chicago
New place to stayLux Loop Retreat: Amazing Views, Free Parking
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 fireplace Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Loft rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with pools Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with lake access Downtown Chicago
- Monthly Rentals Downtown Chicago
- House rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Townhouse rentals Downtown Chicago
- Family-friendly 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