
Family-friendly holiday rentals in Chicago
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Chicago

Total holiday rentals
Explore 5,020 holiday rentals in Chicago

Verified guest reviews
Over 338,690 verified reviews to help you choose

Pet-friendly holiday rentals
Find 1,960 rentals that welcome pets

Holiday rentals with a pool
380 properties feature pools

Rentals with dedicated workspaces
3,410 properties have a dedicated workspace

Wifi availability
4,990 of Chicago holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chicago rentals

4.8 Average rating
Chicago stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Chicago’s top spots include Millennium Park, Wrigley Field and Lincoln Park
Top-rated family-friendly rentals in Chicago
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.
4.99 out of 5 average rating, 118 reviews
West Town 1-Bedroom Full Remodel
Located in the heart of West Town, this 1-bedroom, 1-bath comes equipped with a queen sofa bed and comfortably sleeps 4, plus an in-unit washer/dryer for your convenience. Remodeled in 2023, this stunning unit with 9ft ceilings in a Victorian building is footsteps away from all the amazing bars and restaurants Chicago Ave has to offer. Known for its array of multicultural cuisines, this strip offers everything from Korean fine dining to New Mexican brunch, and is near Chicago’s best attractions!
4.98 out of 5 average rating, 123 reviews
Spacious & Modern Treetop Oasis King Bed + Parking
Take a deep breath and relax in this airy and bright top floor apartment. Treetops surround the newly renovated and spacious home in a premier Oak Park location. 20 min. to downtown Chicago. Only 1/2 block to the FLW Home & Studio. Walk to dining & train. 2 bedrooms & 1 bath w/tub & shower. Open living/dining/kitchen/sunroom. Cook’s kitchen w/huge island. Primary w/king bed + deep closet. 2nd bdrm w/built-in bunk beds + desk + balcony. Private entry & deck. Shared fenced yard. Driveway parking.
4.98 out of 5 average rating, 102 reviews
Charming 3-BED in Lincoln Park/ Old Town & Parking
Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.
4.95 out of 5 average rating, 198 reviews
Beautiful 2BR Apartment in Old Town
Want to experience Chicago neighborhood charms, there is no better place to start than the Old Town Historic District. This 2 bedroom apartment is part of a Victorian-era building while interior has been updated for modern style living. You can enjoy lake front trail in the Summer, Bears football in the Fall, year end holiday shopping in the Winter, and Blackhawks playoffs in the Spring. With both Red and Brown line only a few blocks away, getting around in Chicago does not get any easier.
4.89 out of 5 average rating, 307 reviews
Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
No cleaning fees! Gorgeous gem 10 miles from Downtown, Airport, Lake Michigan, and United Center! 15 miles from Wrigley Field and the Zoo. Next to CTA! 6 bedrooms 2 bathrooms, 10 beds. Sleeps 18 comfortably. Perfect for large groups! Modern smart home with air hockey, pool table, video games, 2 ping pong tables, foosball, 9 big screen TVs including 85" Samsung QLED with surround sound, outdoor dining, charcoal grill, cornhole, dining room, game room, 2 living rooms, and full kitchen.
4.91 out of 5 average rating, 136 reviews
Luxury Loft Collection 01 - Terrace - River North
BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!
4.9 out of 5 average rating, 126 reviews
Fully Furnished Apartment Wicker Park Free Parking
Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available
4.97 out of 5 average rating, 636 reviews
Lakeview Loft-Vintage Chicago, Modern Amenities
The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.
4.96 out of 5 average rating, 608 reviews
Explore Lincoln Park from a Polished Apartment
A bright, cozy, large studio in the heart of Lincoln Park! You enter with a keypad code which we give you a few days prior to your stay. You are steps away from Armitage Ave. and Halsted St. for walkable grocery stores, shops, restaurants and cafes, plus Red and Brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment with free residential parking stickers or an onsite garage space for $25/night.
5.0 out of 5 average rating, 325 reviews
Spacious 1-bedroom South Loop Loft I Sleep 5
Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!
4.94 out of 5 average rating, 250 reviews
Pilsen Modern Chic Retreat
Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.
4.95 out of 5 average rating, 135 reviewsPopular amenities for Chicago family-friendly rentals
Family-friendly home rentals with a hot tub

Private hot tub - King bed suite - Free parking
4.92 out of 5 average rating, 283 reviews
Private Coach house near Lincoln Square!
4.88 out of 5 average rating, 398 reviews
Entire house in Lakeview with yard and garage
4.86 out of 5 average rating, 111 reviews
Modern Getaway w/ Hot Tub, Lrg Yard, Parking
4.96 out of 5 average rating, 187 reviews
Enchanted Garden Treehouse (Amenity*)
4.94 out of 5 average rating, 898 reviews
Ukrainian Village 3BR/3BA • Private Patio, Parking
4.98 out of 5 average rating, 128 reviews
H&H 1896 - Spacious, Fully Stocked, & Free Parking
4.95 out of 5 average rating, 120 reviews
Urban Luxury 1BR/2BA Logan Square Condo w/Garage
4.98 out of 5 average rating, 329 reviewsFamily- and pet-friendly home rentals

Large Home | Free Parking | Near Downtown
4.89 out of 5 average rating, 129 reviews
Newly-renovated historic home in Logan Square
4.99 out of 5 average rating, 180 reviews
Paradise on the Boulevard!
4.99 out of 5 average rating, 112 reviews
Breathtaking & Chic Oasis Loc in Desirable Old Twn
4.87 out of 5 average rating, 179 reviews
The Chicago River House – GIANT wall projector!
4.96 out of 5 average rating, 213 reviews
1,800ft² Parking Workspace W/D Full Kitch
4.99 out of 5 average rating, 223 reviews
Cool City Comfort - Logan Sq. - O’Hare CTA
5.0 out of 5 average rating, 220 reviews
Stylish 2BR stunner w/ unbeatable location
4.92 out of 5 average rating, 209 reviewsFamily-friendly home rentals with a pool

Fun & cozy getaway w/POOL/game room/FREE parking
4.98 out of 5 average rating, 172 reviews
Spectacular 2BR Penthouse in the Loop | Roof Deck
4.81 out of 5 average rating, 360 reviews
50th Floor Mag Mile Views, Balcony, Pool, Gym
4.9 out of 5 average rating, 143 reviews
Highrise Hideout (Fitness Center • Sauna)
4.91 out of 5 average rating, 123 reviews
Whole Flat in Private Club. Walk to L, Dining & Shows
4.9 out of 5 average rating, 600 reviews
"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
4.96 out of 5 average rating, 141 reviews
Cozy Duplex Down in Wicker Park East w/ Parking
4.93 out of 5 average rating, 131 reviews
Just remodeled apartment close to airport and mall
4.91 out of 5 average rating, 128 reviewsWhen is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $185 SGD | $186 SGD | $218 SGD | $223 SGD | $279 SGD | $311 SGD | $277 SGD | $273 SGD | $244 SGD | $247 SGD | $222 SGD | $209 SGD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Destinations to explore
- Indianapolis Holiday rentals
- Columbus Holiday rentals
- St. Louis Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Detroit Holiday rentals
- Milwaukee Holiday rentals
- Traverse City Holiday rentals
- Downtown Chicago Holiday rentals
- Ann Arbor Holiday rentals
- Windsor Holiday rentals
- Grand Rapids Holiday rentals
- Rentals with an accessible-height bed Chicago
- Rentals with lake access Chicago
- Loft rentals Chicago
- Rentals with a sauna Chicago
- Private suite rentals Chicago
- Rentals with breakfast Chicago
- Lakehouse rentals Chicago
- Flat rentals Chicago
- Hotel rooms Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Beachfront rentals Chicago
- Mansion rentals Chicago
- Luxury rentals Chicago
- Bed and breakfasts Chicago
- Boutique hotels Chicago
- House rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Serviced apartment rentals Chicago
- Townhouse rentals Chicago
- Guest house rentals Chicago
- Family-friendly rentals Cook County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- Indiana Dunes State Park
- 875 North Michigan Avenue
- University of Chicago
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Byline Bank Aragon Ballroom
- Donald E Stephens Convention Center
- Frank Lloyd Wright Home and Studio
- Beachwalk Vacation Rentals
- Washington Park Zoo
- Things to do Chicago
- Landmarks Chicago
- Art workshops Chicago
- Museums Chicago
- Food tours Chicago
- Architecture Chicago
- Cultural tours Chicago
- Outdoors Chicago
- Things to do Cook County
- Landmarks Cook County
- Museums Cook County
- Outdoors Cook County
- Cultural tours Cook County
- Architecture Cook County
- Food tours Cook County
- Art workshops Cook County
- Things to do Illinois
- Museums Illinois
- Food tours Illinois
- Art workshops Illinois
- Landmarks Illinois
- Cultural tours Illinois
- Outdoors Illinois
- Architecture Illinois
- Things to do United States
- Shopping and fashion United States
- Dining United States
- Museums United States
- Cultural tours United States
- Architecture United States
- Workouts United States
- Art workshops United States
- Flying United States
- Wellness United States
- Food tours United States
- Wildlife United States
- Landmarks United States
- Water sports United States
- Performances United States
- Tastings United States
- Galleries United States
- Cooking United States
- Outdoors United States
- Beauty United States







