Kid-friendly holiday rentals in Downtown Chicago
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Downtown Chicago
Guests agree: these family-friendly rentals 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
Kid-friendly house rentals
Home in West Town
4.95 out of 5 average rating, 179 reviewsParadise on the Park
Home in Roscoe Village
4.93 out of 5 average rating, 221 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
Home in Berwyn
4.91 out of 5 average rating, 263 reviewsPrivate apartment with retro vibe
Home in Chicago
4.97 out of 5 average rating, 362 reviewsTop Floor Escape | Modern Amenities | Lush Garden
Home in Lake View
4.98 out of 5 average rating, 211 reviewsWrigleyville Southport Studio
Home in Wilmette
4.98 out of 5 average rating, 101 reviewsUnique porcelain-enamel paneled "Lustron" home
Home in Uptown
4.9 out of 5 average rating, 339 reviewsPrivate 3rd Floor Apartment
Home in Chicago
4.96 out of 5 average rating, 208 reviewsDivision St Designer Home In Heart of Wicker Park
Family-friendly apartment rentals
Flat in Chicago
4.84 out of 5 average rating, 178 reviewsLa Casita
Flat in Chicago
4.98 out of 5 average rating, 140 reviewsModern Apt with style & comfort in Pilsen Chicago
Flat in Chicago
5.0 out of 5 average rating, 200 reviewsExplore Lincoln Park from a Polished Apartment
Flat in Avondale
4.97 out of 5 average rating, 125 reviewsDesigner Avondale Attic
Flat in Chicago
4.96 out of 5 average rating, 104 reviewsCute, Clean, Cozy Apartment in Pilsen
Flat in East Rogers Park
4.89 out of 5 average rating, 108 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Flat in Lincoln Park
4.83 out of 5 average rating, 217 reviewsCozy Lincoln Park Studio - Steps to Zoo!
Flat in Chicago
4.89 out of 5 average rating, 250 reviewsModern
Family-friendly apartment rentals
Apartment in Chicago
4.87 out of 5 average rating, 130 reviews3D Tour! Designer Condo near Logan Square
Apartment in Lincoln Square
4.97 out of 5 average rating, 339 reviewsLincoln Square Gem!
Apartment in Chicago
4.86 out of 5 average rating, 341 reviewsNear McCormick Place and Minutes from Downtown!
Apartment in Humboldt Park
4.97 out of 5 average rating, 109 reviewsStylish 3BR + Free Parking 10-15mins from Downtown
Apartment in Lincoln Park
4.96 out of 5 average rating, 448 reviewsUnique Lincoln Park Duplex Apt
Apartment in Chicago
4.99 out of 5 average rating, 578 reviewsUrban Comfort in the Heart of Chicago
Apartment in Chicago
4.96 out of 5 average rating, 181 reviewsUpdated Designer Duplex In Fulton Market W/parking
Apartment in Chicago
4.91 out of 5 average rating, 251 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
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
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Apartment rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
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- Beachfront rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Flat rentals Downtown Chicago
- House rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Monthly Rentals Downtown Chicago
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- Fitness-friendly rentals Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Townhouse rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with pools Downtown Chicago
- Pet-friendly rentals Downtown Chicago
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- Boutique hotel rentals Downtown Chicago
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- Family-friendly rentals Milwaukee
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- 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
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- Holiday Chalets United Kingdom
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- Mansion Rentals United States
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- Holiday Bungalows United Kingdom
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- 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
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