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, 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!
Flat in Near South Side
4.87 out of 5 average rating, 159 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in The Loop
5.0 out of 5 average rating, 4 reviewsThe Playwright's Palace
Apartment in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Flat in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Flat in The Loop
4.81 out of 5 average rating, 27 reviewsThe Professional's Playground
Family- and pet-friendly home rentals
Flat in Irving Park
4.86 out of 5 average rating, 326 reviewsThe Avondale Garden Unit
Flat in Logan Square
4.83 out of 5 average rating, 482 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Evanston
4.77 out of 5 average rating, 569 reviewsSpacious Evanston Unit - Walk to Northwestern U
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Home in Forest Park
4.91 out of 5 average rating, 224 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Guest suite in Wood Dale
4.9 out of 5 average rating, 434 reviewsThe Deer Suite
Flat in Irving Park
4.76 out of 5 average rating, 300 reviewsITALIAN garden apt/kids friendly/great location!!
Flat in Chicago
4.87 out of 5 average rating, 304 reviewsUnwind in the Garden of an elegant, Modern Home
Family-friendly home rentals with a pool
Flat in The Loop
4.78 out of 5 average rating, 189 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
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, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Flat 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
- Flat rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
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- Townhouse rentals Downtown Chicago
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- Waterfront rentals Downtown Chicago
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- House rentals Downtown Chicago
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- Hotel rentals Downtown Chicago
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- Loft rentals Downtown Chicago
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- Rentals with breakfast Downtown Chicago
- Family-friendly rentals Downtown Chicago
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- Yurt Rentals United States
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- Holiday Caravans United Kingdom
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- Farm Houses United States
- Farm Cottages United Kingdom
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- Luxury Cabins United Kingdom
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- Holiday Chalets United Kingdom
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- Holiday Apartments Australia
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- Big House Rentals United States
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- Large Villas United Kingdom
- House Rentals with a Pool United States
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