Family-friendly vacation rentals in Chicago Loop
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chicago Loop
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 Chicago Loop family-friendly rentals
Family-friendly home rentals with a hot tub
Condo in Logan Square
4.98 out of 5 average rating, 235 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apartment in Near South Side
4.8 out of 5 average rating, 56 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Apartment in The Loop
5.0 out of 5 average rating, 4 reviewsThe Playwright's Palace
Family- and pet-friendly home rentals
Apartment in Logan Square
4.89 out of 5 average rating, 341 reviewsSunny Logan Square Artists' home
Apartment in Logan Square
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Lincoln Park
4.89 out of 5 average rating, 145 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Guest suite in Logan Square
4.97 out of 5 average rating, 239 reviewsStylish Studio in Historic Logan Square
Apartment in Irving Park
4.86 out of 5 average rating, 325 reviewsThe Avondale Garden Unit
Apartment in Irving Park
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
Apartment in West Loop
4.93 out of 5 average rating, 214 reviews✨Spacious Centrally Located West Loop Loft✨
Family-friendly home rentals with a pool
Apartment in The Loop
4.77 out of 5 average rating, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Apartment in The Loop
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Apartment in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Place to stay in Berwyn
Beat-Town Flex Stays
Quick stats about vacation rentals that are family-friendly in Chicago Loop
Total rentals
270 properties
Wifi availability
260 properties include access to wifi
Rentals with dedicated workspaces
190 properties have a dedicated workspace
Rentals with a pool
150 properties have a pool
Pet-friendly rentals
120 properties allow pets
Total number of reviews
8.6K reviews
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a patio Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Monthly Rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Loft rentals Chicago Loop
- Condo rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with lake access Chicago Loop
- Hotel rentals Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with pools Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with an EV charger Chicago Loop
- Apartment rentals Chicago Loop
- Kid-friendly rentals Chicago Loop
- Rentals with breakfast Chicago Loop
- Rentals with a fireplace Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with beach access Chicago Loop
- Rentals with a hot tub Chicago Loop
- Family-friendly rentals Illinois
- 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