Family-friendly vacation rentals in Northwest Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Northwest 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 Northwest Side family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov. 12 – 19
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov. 1 – 8
Condo in Chicago
4.98 out of 5 average rating, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Sep. 12 – 19
Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsThe Professional's Playground
Nov. 17 – 24
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jun. 5 – 12
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Oct. 12 – 19
Condo in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Mar. 15 – 22
Apartment in Chicago
New place to stayThe Playwright's Palace
Jan. 12 – 19
Family- and pet-friendly home rentals
Apartment in Chicago
4.76 out of 5 average rating, 298 reviewsITALIAN garden apt/kids friendly/great location!!
Oct. 25 – Nov. 1
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Jan. 14 – 21
Apartment in Forest Park
4.92 out of 5 average rating, 112 reviewsVillage Cottage - Forest Park Studio Pets 72142F
May 7 – 14
Condo in Evanston
4.76 out of 5 average rating, 567 reviewsSpacious Evanston Unit - Walk to Northwestern U
Feb. 18 – 25
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jun. 25 – Jul. 2
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 294 reviewsa SIMPLE place
Jan. 6 – 13
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Apr. 13 – 20
Condo in Chicago
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Sep. 13 – 20
Family-friendly home rentals with a pool
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
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Jan. 3 – 10
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Nov. 23 – 30
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Aug. 5 – 12
Apartment in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Feb. 12 – 19
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar. 11 – 18
Place to stay in Berwyn
Beat-Town Flex Stays
Dec. 24 – 31
Destinations to explore
- Downtown Chicago Vacation rentals
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