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 Chicago
4.98 out of 5 average rating, 232 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Jan 4 – 11
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, 155 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)
Mar 31 – Apr 7
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
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 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 Wicker Park
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Oct 14 – 21
Apartment in Chicago
4.74 out of 5 average rating, 186 reviewsCozy Bedroom in Wrigleyville (Entire Apt)
Apr 7 – 14
Condo in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
Oct 27 – Nov 3
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Sep 25 – Oct 2
Guest suite in Chicago
4.97 out of 5 average rating, 237 reviewsStylish Studio in Historic Logan Square
Sep 17 – 24
Apartment in Chicago
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Apr 4 – 11
Condo in Chicago
4.88 out of 5 average rating, 234 reviews2 King Bed Condo Easy Downtown Free Street Parking
Sep 8 – 15
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
Feb 8 – 15
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
Feb 1 – 8
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
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Sep 11 – 18
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 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
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