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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
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Apartment in Chicago
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
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Home in Chicago
4.85 out of 5 average rating, 296 reviewsLux Urban 3BR/3BA Duplex + Parking!
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Rental unit in Chicago
4.87 out of 5 average rating, 175 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
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Rental unit in Chicago
4.73 out of 5 average rating, 33 reviewsThe Professional's Playground
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Apartment in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
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Loft in Chicago
4.81 out of 5 average rating, 280 reviewsArtist Loft Duplex in a 1904 Former Factory
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Rental unit in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
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Rental unit in Chicago
5 out of 5 average rating, 4 reviewsLux Loop Retreat: Amazing Views, Free Parking
Family- and pet-friendly home rentals
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Rental unit in Chicago
4.92 out of 5 average rating, 156 reviewsUrban Pilsen Apt. near Downtown
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Rental unit in Chicago
4.76 out of 5 average rating, 309 reviewsITALIAN garden apt/kids friendly/great location!!
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Apartment in Evanston
4.77 out of 5 average rating, 583 reviewsSpacious Evanston Unit - Walk to Northwestern U
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Guest suite in Chicago
4.94 out of 5 average rating, 131 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
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Rental unit in Chicago
4.87 out of 5 average rating, 285 reviewsLogan Square Video Game Loft
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Home in Forest Park
4.9 out of 5 average rating, 235 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
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Rental unit in Chicago
4.92 out of 5 average rating, 408 reviewsAndersonville Living
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Home in Chicago
4.89 out of 5 average rating, 342 reviewsPrivate 3rd Floor Apartment
Family-friendly home rentals with a pool
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Rental unit in Chicago
4.77 out of 5 average rating, 212 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
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Rental unit in Chicago
5 out of 5 average rating, 11 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
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Guest suite in Berwyn
4.71 out of 5 average rating, 34 reviewsMusic Hot Spot’s Main Level
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Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
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Rental unit in Chicago
4.76 out of 5 average rating, 194 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
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Place to stay in Berwyn
Beat-Town Flex Stays
Destinations to explore
- Milwaukee Holiday rentals
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