Family-friendly holiday 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.
Holiday 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, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
6–13 Jan
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
3–10 Sep
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
1–8 Jan
Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsThe Professional's Playground
17–24 Nov
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
5–12 Jul
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
11–18 Sep
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
11–18 Oct
Apartment in The Loop
New place to stayThe Playwright's Palace
7–14 Oct
Family- and pet-friendly home rentals
Apartment in Irving Park
4.76 out of 5 average rating, 298 reviewsITALIAN garden apt/kids friendly/great location!!
25 Oct – 1 Nov
Apartment in Irving Park
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
28 Feb – 7 Mar
Apartment in Wicker Park
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
17–24 Oct
Guest suite in Wood Dale
4.9 out of 5 average rating, 429 reviewsThe Deer Suite
17–24 Oct
Guest suite in Portage Park
4.95 out of 5 average rating, 120 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
15–22 Feb
Condo in Evanston
4.76 out of 5 average rating, 567 reviewsSpacious Evanston Unit - Walk to Northwestern U
5–12 Jan
Apartment in Chicago
4.92 out of 5 average rating, 396 reviewsAndersonville Living
20–27 Sep
Condo in West Town
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
31 Oct – 7 Nov
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
8–15 Feb
Apartment in The Loop
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
8–15 Apr
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
17–24 Jan
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
24–31 Jul
Apartment in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
11–18 Sep
Apartment in The Loop
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
24–31 Mar
Place to stay in Berwyn
Beat-Town Flex Stays
1–8 Dec
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston 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
- Family-friendly rentals Downtown Chicago
- Family-friendly rentals Illinois
- Beachfront rentals North Side
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- Bed and breakfasts North Side
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- Condo rentals North Side
- Guesthouse rentals North Side
- Rentals with a hot tub North Side
- Monthly Rentals North Side
- Loft rentals North Side
- Rentals with an EV charger North Side
- Rentals with a fireplace North Side
- Townhouse rentals North Side
- Rentals with pools North Side
- Private suite rentals North Side
- House rentals North Side
- Pet-friendly rentals North Side
- Rentals with breakfast North Side
- Apartment rentals North Side
- Rentals with outdoor seating North Side
- Rentals with beach access North Side
- Hotel rentals North Side
- Rentals with lake access North Side
- Fitness-friendly rentals North Side
- Kid-friendly rentals North Side
- Rentals with a patio North Side
- Rentals with a washing machine and dryer North Side
- Yurt Rentals United States
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