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
Condo in Chicago
4.98 out of 5 average rating, 235 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 Near South Side
4.87 out of 5 average rating, 159 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in The Loop
4.81 out of 5 average rating, 27 reviewsThe Professional's Playground
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Condo in Chicago
4.46 out of 5 average rating, 79 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Family- and pet-friendly home rentals
Apartment in Irving Park
4.86 out of 5 average rating, 327 reviewsThe Avondale Garden Unit
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Logan Square
4.83 out of 5 average rating, 482 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Home in Forest Park
4.91 out of 5 average rating, 224 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Apartment in Chicago
4.75 out of 5 average rating, 190 reviewsCozy Bedroom in Wrigleyville (Entire Apt)
Condo in Evanston
4.77 out of 5 average rating, 569 reviewsSpacious Evanston Unit - Walk to Northwestern U
Apartment in Irving Park
4.76 out of 5 average rating, 301 reviewsITALIAN garden apt/kids friendly/great location!!
Apartment in Lincoln Park
4.88 out of 5 average rating, 146 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Family-friendly home rentals with a pool
Apartment in The Loop
4.77 out of 5 average rating, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
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
Apartment in The Loop
4.78 out of 5 average rating, 189 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Apartment in The Loop
4.62 out of 5 average rating, 50 reviewsStylish 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
- Loft rentals Downtown Chicago
- Rentals with pools Downtown Chicago
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- Condo rentals Downtown Chicago
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- House rentals Downtown Chicago
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- Townhouse rentals Downtown Chicago
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- Family-friendly rentals Lake Geneva
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- Yurt Rentals United States
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- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
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- Holiday Chalets United Kingdom
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- Holiday Apartments Australia
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- Private Holiday Rentals United Kingdom
- Big House Rentals United States
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- Large Villas United Kingdom
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