
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.

Explore Lincoln Park from a Polished Apartment
This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.
KitchenFamilyBathroom
5.0 out of 5 average rating, 321 reviews
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.
Indoor spacesKitchenNearby
4.99 out of 5 average rating, 111 reviews
LIVN Millennium Park Downtown Chicago 1 BR
Experience the best of Chicago from this stylish, newly renovated 1-bedroom at 19 S Wabash Ave. Perfectly located in the heart of downtown, you'll be steps away from iconic Millennium Park, the vibrant shops of Michigan Avenue, and a world of dining options. This 1 bedroom offers modern comfort with a fully equipped kitchen, including a refrigerator, dishwasher, and coffee maker, plus the convenience of an in-unit washer and dryer, making it ideal for both short getaways and extended stays. Enjo
Indoor spacesFamilySleep quality
4.88 out of 5 average rating, 146 reviews
Luxury SOHO Styled Two-Level Townhouse - Old Town
NEWLY CONSTRUCTED TOWNHOUSE IN THE HEART OF OLD TOWN! This private luxury townhouse (duplex) is perfectly located in vibrant Old Town-surrounded by nightlife, restaurants, cultural attractions, and is only a 5 min walk to the beach, steps from Lincoln Park, and next to Second City. This 2,800 square foot townhouse features 13 foot ceilings, open floorplan, private patio, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between.
Indoor spacesKitchenAccess
4.94 out of 5 average rating, 161 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.
FamilyIndoor spacesLaundry
4.95 out of 5 average rating, 195 reviews
Chic 2BR Gem with Fireplace
Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***
KitchenFamilyParks
4.98 out of 5 average rating, 164 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.
Indoor spacesFamilyHospitality
4.89 out of 5 average rating, 304 reviews
Kasa | Views from your Private Balcony | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.
KitchenFamilyAccess
4.81 out of 5 average rating, 1040 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.
KitchenFamilyBiking
4.96 out of 5 average rating, 602 reviews
Entire first floor in Lincoln Square!
First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!
FamilyKitchenParking
4.99 out of 5 average rating, 152 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.
KitchenIndoor spacesCondition
4.95 out of 5 average rating, 132 reviews
Bright family-friendly Lincoln Square 2-bed 1-bath
Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.
FamilyIndoor spacesValue
4.95 out of 5 average rating, 442 reviewsPopular amenities for Chicago family-friendly rentals
Family-friendly home rentals with a hot tub

Private Coach house near Lincoln Square!
KitchenFamilyGrill
4.88 out of 5 average rating, 394 reviews
Private hot tub - King bed suite - Free parking
FamilyKitchenHeating
4.93 out of 5 average rating, 281 reviews
Ukrainian Village 3BR/3BA • Private Patio, Parking
Indoor spacesFamilyNearby
4.98 out of 5 average rating, 125 reviews
Enchanted Garden Treehouse (Amenity*)
KitchenIndoor spacesWifi
4.94 out of 5 average rating, 892 reviews
Entire house in Lakeview with yard and garage
Indoor spacesKitchenHospitality
4.86 out of 5 average rating, 111 reviews
Modern Getaway w/ Hot Tub, Lrg Yard, Parking
Indoor spacesFamilyGetting around
4.96 out of 5 average rating, 182 reviews
Tea Studio in Wicker Park Spring Factory
FamilyKitchenHot tub
4.96 out of 5 average rating, 307 reviews
Checkerboard Studio, Private Outdoor Hot Tub, Yard
FamilyKitchenBack garden
4.86 out of 5 average rating, 537 reviewsFamily- and pet-friendly home rentals

Newly-renovated historic home in Logan Square
FamilyKitchenOutdoor spaces
4.99 out of 5 average rating, 176 reviews
3-bedroom exposed brick in Chicago's Wicker Park
FamilyKitchenView
4.98 out of 5 average rating, 167 reviews
Beautiful, sunny 2nd floor 3BR/1BA w free parking
Indoor spacesFamilyAir conditioning
4.93 out of 5 average rating, 175 reviews
1,800ft² Parking Workspace W/D Full Kitch
FamilyKitchenWifi
4.99 out of 5 average rating, 222 reviews
Historic Old Town, Fabulous 4 Bedroom Home
FamilyKitchenCondition
4.87 out of 5 average rating, 210 reviews
Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
KitchenFamilyLaundry
4.91 out of 5 average rating, 133 reviews
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
KitchenIndoor spacesAmenities
4.94 out of 5 average rating, 582 reviews
Modern 1BR in Little Italy, Near West Loop
FamilyIndoor spacesAccuracy
4.9 out of 5 average rating, 174 reviewsFamily-friendly home rentals with a pool

Fun & cozy getaway w/POOL/game room/FREE parking
Indoor spacesFamilyDecor
4.98 out of 5 average rating, 172 reviews
Gold Coast Luxury: 2BR with Sweeping City Vistas
KitchenFamilyLocation
4.94 out of 5 average rating, 125 reviews
Professional's Playground (Fitness Center • Sauna)
Indoor spacesFamilyTV
4.92 out of 5 average rating, 129 reviews
Spectacular 2BR Penthouse in the Loop | Roof Deck
KitchenFamilyGrill
4.81 out of 5 average rating, 355 reviews
Just remodeled apartment close to airport and mall
FamilyIndoor spacesQuiet
4.92 out of 5 average rating, 124 reviews
Whole Flat in Private Club. Walk to L, Dining & Shows
FamilyKitchenQuiet
4.9 out of 5 average rating, 600 reviews
Harmony of Evanston 1 BDR Exec Suite w/pool & Gym
FamilyKitchenHospitality
4.96 out of 5 average rating, 146 reviews
Cozy Duplex Down in Wicker Park East w/ Parking
KitchenIndoor spacesQuiet
4.93 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 | $276 SGD | $272 SGD | $243 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
- Luxury rentals Chicago
- Hotel rooms Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Beachfront rentals Chicago
- Mansion rentals Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Boutique hotels Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Serviced apartment rentals Chicago
- Townhouse rentals Chicago
- Guest house rentals Chicago
- Flat 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
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Beachwalk Vacation Rentals
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- 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
- Museums United States
- Dining 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
- Performances United States
- Tastings United States
- Galleries United States
- Cooking United States
- Beauty United States
- Outdoors United States
- Water sports United States







