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Family-friendly vacation rentals in Chicago Loop
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chicago Loop
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago Loop family-friendly rentals
Family-friendly home rentals with a hot tub
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Condo in Logan Square
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
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Home in West Town
4.85 out of 5 average rating, 296 reviewsLux Urban 3BR/3BA Duplex + Parking!
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Rental unit in Near South Side
4.87 out of 5 average rating, 175 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
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Rental unit in The Loop
4.73 out of 5 average rating, 33 reviewsThe Professional's Playground
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Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
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Loft in West Town
4.81 out of 5 average rating, 280 reviewsArtist Loft Duplex in a 1904 Former Factory
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Rental unit in Bronzeville
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
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Rental unit in Near South Side
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 Logan Square
4.83 out of 5 average rating, 494 reviewsRelaxed Bucktown/Wicker Park 1B Apt
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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 Irving Park
4.76 out of 5 average rating, 309 reviewsITALIAN garden apt/kids friendly/great location!!
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Guest suite in Logan Square
4.97 out of 5 average rating, 251 reviewsStylish Studio in Historic Logan Square
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Rental unit in Logan Square
4.87 out of 5 average rating, 285 reviewsLogan Square Video Game Loft
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Rental unit in West Town
4.87 out of 5 average rating, 310 reviewsUnwind in the Garden of an elegant, Modern Home
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Condo in Evanston
4.77 out of 5 average rating, 583 reviewsSpacious Evanston Unit - Walk to Northwestern U
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Home in Uptown
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 The Loop
4.76 out of 5 average rating, 194 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
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Rental unit in The Loop
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 Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
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Rental unit in The Loop
4.77 out of 5 average rating, 212 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
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Place to stay in Berwyn
Beat-Town Flex Stays
Quick stats about vacation rentals that are family-friendly in Chicago Loop
Total rentals
270 properties
Total number of reviews
9K reviews
Pet-friendly rentals
130 properties allow pets
Rentals with a pool
150 properties have a pool
Rentals with dedicated workspaces
200 properties have a dedicated workspace
Wifi availability
270 properties include access to wifi
Destinations to explore
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