
Family-friendly holiday rentals in Chicago
Find and book unique family-friendly homes on Airbnb
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.

Private Lincoln Square one bed+bath studio apt.
Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

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.

A bit of the North Woods on Chicago's North Side!
Looking to get away from it all but not TOO far away? Ours is a quiet, screen-free property perfect for a writer’s or artist’s retreat. NU/Loyola parents or alums, stay here when you visit your kids/alma mater. Fantastic renovated livery barn with lots of light, privacy and amenities. Located in Rogers Park, a short walk to Metra and the Red line. Ample street parking nearby. Created for comfort with a splash of Swedish design, enjoy the deck overlooking a tree-filled garden and waterfall.

Grace House | Cozy, contemporary + convenient 2-BR
Make yourself at home in our newly renovated, spacious and immaculately clean 2-bedroom, 1-bath condo — perfect for your next family, work or friends' trip. Located on a tree-lined street in a family-friendly neighborhood and walkable to shops, restaurants, cafes, bars and more. A stone's throw to Southport Corridor/Wrigleyville/Lakeview, Lincoln Square, Roscoe Village and everything the Northside has to offer. Gigabit internet w/ WiFi and everything you need to live and thrive in Chicago.

A guest suite centrally located, but so quiet
IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my private guest suite w/kitchenette, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Cozy 3BR on Chicago's North Side & Free Parking
Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Penthouse Near Wrigley Field
This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

Best in Chicago, private, amazing garden space
We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

Old Town Condo with Parking and Terrace
Experience Chicago from my light-filled 2-bed, 2-bath Old Town condo for 4. This urban retreat boasts 13-ft ceilings, a private terrace, dedicated workspace, and gourmet kitchen. Steps from Wells Street's best dining, Second City, Lincoln Park and North Avenue Beach. Perfect for families or professionals seeking a stylish city base with included parking in elevator building.

Elegant Suite in Gold Coast
Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of May 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours***
Popular amenities for Chicago family-friendly rentals
Family-friendly home rentals with a hot tub

Top Floor Views + Central Comfort

Private Coach house near Lincoln Square!

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

Tea Studio in Wicker Park Spring Factory

The Spa of Downtown Whiting

Belmont Pleasures - hot tub / arcade gaming room

Checkerboard Studio, Private Outdoor Hot Tub, Yard

Private hot tub - King bed suite - Free parking
Family- and pet-friendly home rentals

Wicker Park Walk-Up Condo

Archways at the Lincoln Park Zoo 2bed/2ba

ALOHA Tropical Penthouse in Wicker Park Sleeps 14

Private 3rd Floor Apartment

Lincoln Square Gem!

RetroModern Bungalow | free parking | pet friendly

Susie's Space. 2BR easy parking & pet friendly

Cozy Lakeview Apt-Walk to Wrigley & Free Parking!
Family-friendly home rentals with a pool

Level ◆ Brand New Luxe One Bedroom

Upscale High-Rise Apt · Rooftop Pool + Views

Munster hide away

Whole Flat in Private Club. Walk to L, Dining & Shows

Elmhurst 4BR Home with Pool | Mid-Term Ready

50th Floor Mag Mile Views, Balcony, Pool, Gym

Andersonville Luxury Pool Escape

Sentral Studio Apt in South Loop Chicago
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $186 SGD | $187 SGD | $212 SGD | $219 SGD | $253 SGD | $268 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 |
Quick stats about holiday rentals that are family-friendly in Chicago

Total holiday rentals
Explore 5,510 holiday rentals in Chicago

Verified guest reviews
Over 323,050 verified reviews to help you choose

Pet-friendly holiday rentals
Find 2,050 rentals that welcome pets

Holiday rentals with a pool
390 properties feature pools

Rentals with dedicated workspaces
3,840 properties have a dedicated workspace

Wifi availability
5,460 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
Destinations to explore
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- 875 North Michigan Avenue
- Soldier Field
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- University of Chicago
- Washington Park Zoo
- Things to do Chicago
- Sightseeing Chicago
- Nature and outdoors Chicago
- Tours Chicago
- Food and drink Chicago
- Sports activities Chicago
- Art and culture Chicago
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