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
Condo in Chicago
4.98 out of 5 average rating, 232 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Jan. 5 – 12
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Aug. 31 – Sep. 7
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Oct. 4 – 11
Apartment in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
Jan. 2 – 9
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul. 5 – 12
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Nov. 2 – 9
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Sep. 5 – 12
Apartment in The Loop
New place to stayThe Playwright's Palace
Jun. 27 – Jul. 4
Family- and pet-friendly home rentals
Apartment in Chicago
4.76 out of 5 average rating, 298 reviewsITALIAN garden apt/kids friendly/great location!!
Dec. 11 – 18
Apartment in Chicago
4.74 out of 5 average rating, 187 reviewsCozy Bedroom in Wrigleyville (Entire Apt)
Apr. 13 – 20
Apartment in Chicago
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Apr. 4 – 11
Apartment in Wicker Park
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct. 5 – 12
Condo in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec. 2 – 9
Apartment in Chicago
4.92 out of 5 average rating, 396 reviewsAndersonville Living
Oct. 3 – 10
Guest suite in Wood Dale
4.9 out of 5 average rating, 427 reviewsThe Deer Suite
Oct. 17 – 24
Guest suite in Chicago
4.95 out of 5 average rating, 119 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
Nov. 29 – Dec. 6
Family-friendly home rentals with a pool
Apartment in The Loop
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Feb. 8 – 15
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Jan. 12 – 19
Apartment in Forest Park
4.91 out of 5 average rating, 11 reviewsComfy & Cute-Oak Park Area - Parking +Public Trans
Sep. 1 – 8
Apartment in The Loop
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Feb. 12 – 19
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Apr. 17 – 24
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Dec. 15 – 22
Apartment in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Sep. 11 – 18
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar. 24 – 31
Destinations to explore
- Downtown Chicago Vacation rentals
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