
Family-friendly holiday rentals in Cook County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Cook County
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.

Best Deal in Chicago | Great Food & Free Parking
Clean & modern Avondale apt close to Blue Line, perfect for urban explorers! Stylish decor, comfy bed, and a cozy ambiance await. Explore nearby cafes, bars, and boutiques, or hop on the train for downtown adventures. Easy to access & great neighborhood. Easy permit parking (free passes provided) on street allows for the ability to drive or take public transportation wherever you want to explore. Avondale has been voted one of the best neighborhoods in Chicago! Come see what the fuss is about.

Fairfield Flat, Airy Vintage Rehab
This remodeled first floor apartment is close to the California Pink Line Station, Pete's Fresh Market, and Douglass Park. Pilsen and West Loop night life a short train ride away. Situated in a quiet corner of Little Village, our neighborhood of predominately Mexican and Black multi-generational families is teeming with tamale stands, paleta vendors, and children playing. Great for couples or friends, though parents have expressed frustration with the hard, or uneven surfaces, and the stairs.

Comfy, 1 Bedroom Apt. w/ Kitchen & Parking for 4
Enjoy our historic district three-flat w/ free parking in upscale, safe Oak Park just 3 blocks to the train, easy access to Chicago. Enjoy some tranquil time in our little eco suburban farm. Check out the gardens and visit our 6 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Humboldt Park Loft
Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Bright Cozy Modern-Chic Condo in Trendy West Town
Kick back & relax in your home away from home in our luxurious, spacious and peaceful abode in the heart of the West Town & Noble Square neighborhoods, close to downtown. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Grand Avenue, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Retro Modern Bungalow | free parking | fire pit
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Feelin’ Blue-tiful • Vintage 1 BR Near Wrigley
Blue by choice, not accident. Feelin' Blue-tiful is a bold Chicago apartment in the dead middle of prime Wrigleyville, just steps from Wrigley Field, the Red Line, and Clark Street. An ideal spot for guests who want comfort, style, and walkability in one of Chicago’s most lively North Side neighborhoods. Striking blue tones, curated art, and plenty of light give this space a memorable, design-forward vibe that is perfect for guests who want a unique stay near the ballpark.

Downtown Park #11 - Mich Ave PH | gym+rooftop
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Cozy guest studio, great for couples!
This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Funky & newly remodeled 1 bed in Hip Logan Square
Recently remodeled 1 bedroom garden apartment with a fun aesthetic in hip Logan Square. Walking distance to top bars, restaurants and coffee shops such as Sugarmoon, Park & Field, Best Intentions, Lou Malnatis, Damn Fine Coffee Bar and many more. Blocks from the 606 Trail, 90/94 & public transportation. Lovely shared front yard landscaped with florals + garden beds. We will pass along a welcome guide with a list of all our favorite places in the neighborhood!

Great location. Free parking.
Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.
Popular amenities for Cook County family-friendly rentals
Family-friendly home rentals with a hot tub

Private Coach house near Lincoln Square!

Modern Lux 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

Enchanted Garden Treehouse (Amenity*)
Family- and pet-friendly home rentals

Peaceful Portage Park Apartment

Sunny Logan Square Artists' home

Picture Perfect 3Bed Steps from Train and FLW

Less is more! Pet friendly Tiny Home near Chicago!

Eddy Street Upstairs Apartment

Garden on Warren

Downtown & UC Nearby · Transit at Your Door

Elegant Suite in Gold Coast
Family-friendly home rentals with a pool

Romantic Spa Getaway -Private Jacuzzi, Sauna, Pool

The Metropolitan Retreat (Fitness Center • Sauna)

Top of River West: Luxe Penthouse for Groups

Stunning 3BR Penthouse in the Loop | Roof Deck

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

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Elmhurst 4BR Home with Pool | Mid-Term Ready

50th Floor Mag Mile Views, Balcony, Pool, Gym
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- Family-friendly rentals Illinois
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Soldier Field
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Oak Street Beach
- Garfield Park Conservatory
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- The 606
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