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, 171 reviewsParadise on the Park
14–21 Jan
Home in Uptown
4.89 out of 5 average rating, 333 reviewsPrivate 3rd Floor Apartment
11–18 Feb
Home in West Loop
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
24–29 Dec
Home in Berwyn
4.91 out of 5 average rating, 242 reviewsPrivate apartment with retro vibe
8–15 Sept
Home in Avondale
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
9–16 Feb
Home in Bridgeport
4.95 out of 5 average rating, 122 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
4–11 Jul
Home in Lake View
4.98 out of 5 average rating, 206 reviewsWrigleyville Southport Studio
25 Nov – 2 Dec
Home in Chicago
4.97 out of 5 average rating, 357 reviewsGreystone Haven in Logan Square
17–24 Oct
Family-friendly apartment rentals
Flat in Chicago
4.86 out of 5 average rating, 103 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
4–11 Apr
Flat in Chicago
4.84 out of 5 average rating, 176 reviewsLa Cottage
25 Sept – 2 Oct
Flat in Uptown
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
18–25 Oct
Flat in Lincoln Square
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
20–27 Nov
Flat in East Rogers Park
4.89 out of 5 average rating, 106 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
14–21 Apr
Flat in West Town
4.96 out of 5 average rating, 263 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
20–27 Jan
Flat in Logan Square
4.92 out of 5 average rating, 492 reviews2BR Bursting w/ Character in Hip Logan Square!
27 Mar – 3 Apr
Flat in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
14–21 Jul
Family-friendly apartment rentals
Apartment in West Town
4.87 out of 5 average rating, 108 reviewsSpacious Duplex in Great Location
3–10 Oct
Apartment in West Town
4.86 out of 5 average rating, 191 reviewsBold Ukrainian Village 2 Bedroom w/Garage Parking
11–18 Dec
Apartment in Chicago
4.95 out of 5 average rating, 131 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Apartment in Humboldt Park
4.86 out of 5 average rating, 125 reviews3D Tour! Designer Condo near Logan Square
29 Sept – 6 Oct
Apartment in Humboldt Park
4.97 out of 5 average rating, 101 reviewsStylish 3BR + Free Parking 10-15mins from Downtown
2–9 Oct
Apartment in Lincoln Park
4.95 out of 5 average rating, 441 reviewsUnique Lincoln Park Duplex Apt
27 Oct – 3 Nov
Apartment in West Loop
4.96 out of 5 average rating, 178 reviewsUpdated Designer Duplex In Fulton Market W/parking
8–15 Jan
Apartment in Chicago
4.92 out of 5 average rating, 248 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
4–11 Apr
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
- Beachfront rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- House rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with beach access Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with pools Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
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- Rentals with a firepit Downtown Chicago
- Family-friendly rentals Milwaukee
- Family-friendly rentals Lake Geneva
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- Family-friendly rentals Cook County
- Yurt Rentals United States
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- Castle Rentals United States
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- Holiday Caravans United Kingdom
- Private Island Rentals United States
- 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 Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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