Family-friendly vacation rentals in South Loop, Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in South Loop, 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 South Loop, Chicago 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
Sep 12 – 19
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov 22 – 29
Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsThe Professional's Playground
Nov 17 – 24
Condo in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Mar 15 – 22
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Oct 13 – 20
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jun 5 – 12
Condo in Bronzeville
4.46 out of 5 average rating, 79 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Jun 3 – 10
Family- and pet-friendly home rentals
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Feb 10 – 17
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Feb 8 – 15
Guest suite in Logan Square
4.97 out of 5 average rating, 238 reviewsStylish Studio in Historic Logan Square
Oct 4 – 11
Home in Uptown
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Jan 8 – 15
Apartment in Pilsen Historic District
4.9 out of 5 average rating, 154 reviewsSpacious unique artist's home in Pilsen
Oct 20 – 27
Condo in West Town
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Feb 16 – 23
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Nov 30 – Dec 7
Apartment in Chicago
4.87 out of 5 average rating, 304 reviewsUnwind in the Garden of an elegant, Modern Home
Apr 16 – 23
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
Apartment in Chicago
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Jun 23 – 30
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Aug 6 – 13
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Nov 12 – 19
Apartment in The Loop
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Nov 26 – Dec 3
Apartment in The Loop
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
Feb 1 – 8
Quick stats about vacation rentals that are family-friendly in South Loop, Chicago
Total rentals
240 properties
Rentals with dedicated workspaces
190 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
50 properties allow pets
Total number of reviews
9.2K reviews
Nightly prices starting at
$80 before taxes and fees
Destinations to explore
- Family-friendly rentals United States
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- Rentals with an EV charger South Loop
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