Family-friendly vacation rentals in North Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in North Side
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 North Side family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chicago
4.85 out of 5 average rating, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
Condo in Chicago
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Apartment in Chicago
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in Chicago
4.83 out of 5 average rating, 29 reviewsThe Professional's Playground
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Apartment in Chicago
New place to stayLux Loop Retreat: Amazing Views, Free Parking
Family- and pet-friendly home rentals
Apartment in Chicago
4.83 out of 5 average rating, 484 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Irving Park
4.86 out of 5 average rating, 329 reviewsThe Avondale Garden Unit
Condo in West Town
4.97 out of 5 average rating, 716 reviewsGreat location. Free parking.
Apartment in Chicago
4.76 out of 5 average rating, 302 reviewsITALIAN garden apt/kids friendly/great location!!
Apartment in Lincoln Park
4.89 out of 5 average rating, 149 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Home in Chicago
4.9 out of 5 average rating, 338 reviewsPrivate 3rd Floor Apartment
Apartment in Chicago
4.96 out of 5 average rating, 349 reviewsLovely, bright, 3-bedroom Avondale flat. Private.
Home in Forest Park
4.91 out of 5 average rating, 225 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Family-friendly home rentals with a pool
Apartment in Chicago
4.77 out of 5 average rating, 191 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
Apartment in Chicago
4.77 out of 5 average rating, 206 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Apartment 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
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