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 14 – 21
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 15 – 22
Condo in Chicago
4.98 out of 5 average rating, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Mar 18 – 25
Apartment in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Nov 17 – 24
Home in Miller Beach
4.54 out of 5 average rating, 150 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Apr 23 – 30
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Jun 13 – 20
Condo in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Mar 21 – 28
Family- and pet-friendly home rentals
Apartment in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
Mar 18 – 25
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Oct 15 – 22
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec 2 – 9
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jun 23 – 30
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 294 reviewsa SIMPLE place
Feb 19 – 26
Apartment in Chicago
4.95 out of 5 average rating, 654 reviewsBest in Chicago, private, amazing garden space
Oct 29 – Nov 5
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Dec 18 – 25
Apartment in Chicago
4.92 out of 5 average rating, 397 reviewsAndersonville Living
Oct 3 – 10
Family-friendly home rentals with a pool
Apartment in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Dec 14 – 21
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Apr 8 – 15
Apartment in Chicago
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Apr 12 – 19
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Dec 18 – 25
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Aug 8 – 15
Apartment in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Nov 26 – Dec 3
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
Mar 4 – 11
Destinations to explore
- Downtown Chicago Vacation rentals
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- Family-friendly rentals Cook County
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