Family-friendly vacation rentals in Woodlawn, Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Woodlawn, Chicago
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 Woodlawn, Chicago 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
4.86 out of 5 average rating, 154 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 2 – 9
Apartment in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
Jan 2 – 9
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 4 – 11
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
Apartment in The Loop
New place to stayThe Playwright's Palace
Nov 29 – Dec 6
Family- and pet-friendly home rentals
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Feb 9 – 16
Apartment in Irving Park
4.76 out of 5 average rating, 296 reviewsITALIAN garden apt/kids friendly/great location!!
Feb 25 – Mar 4
Apartment in Chicago
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Apr 4 – 11
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Jul 16 – 23
Condo in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec 2 – 9
Guest suite in Wood Dale
4.9 out of 5 average rating, 427 reviewsThe Deer Suite
Oct 17 – 24
Apartment in Wicker Park
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct 14 – 21
Guest suite in Chicago
4.97 out of 5 average rating, 237 reviewsStylish Studio in Historic Logan Square
Sep 25 – Oct 2
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 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 12 – 19
Apartment in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Feb 8 – 15
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar 24 – 31
Place to stay in Berwyn
Beat-Town Flex Stays
Nov 27 – Dec 4
Quick stats about vacation rentals that are family-friendly in Woodlawn, Chicago
Total rentals
100 properties
Wifi availability
100 properties include access to wifi
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
3.6K reviews
Nightly prices starting at
€ 37 before taxes and fees
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Family-friendly rentals Illinois
- Kid-friendly rentals Woodlawn
- Condo rentals Woodlawn
- Rentals with beach access Woodlawn
- Rentals with lake access Woodlawn
- Rentals with outdoor seating Woodlawn
- Monthly Rentals Woodlawn
- House rentals Woodlawn
- Rentals with a fireplace Woodlawn
- Pet-friendly rentals Woodlawn
- Apartment rentals Woodlawn
- Rentals with a washer and dryer Woodlawn
- Rentals with a patio Woodlawn
- Family-friendly rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom