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Family-friendly vacation 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.

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Top guest favorite

Apartment in Chicago

5 out of 5 average rating, 279 reviews

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.

Top guest favorite

The living area features a cozy sofa and a patterned armchair, complemented by a glass coffee table. A television is positioned in one corner. Large windows invite natural light, while floor-to-ceiling curtains offer privacy. A potted plant adds a touch of greenery.

Home in Wilmette

4.98 out of 5 average rating, 166 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Top guest favorite

An inviting living area features a cozy sofa and an accent chair arranged thoughtfully around a decorative table. A vintage fireplace with intricate tile work serves as a focal point, accented by houseplants and framed artwork. Warm wooden flooring enhances the bright, airy ambiance.

Apartment in Chicago

4.99 out of 5 average rating, 110 reviews

Plants and Art | Near Trendy Restaurants & Bars

Light-Filled Apartment Near Chicago’s Best Restaurants & Bars • Friends & Couples • A/C • Coffee Station w/Local Beans • Fully-Equipped Kitchen Whether you’re in town to explore or unwind, you’ll love the proximity to restaurants, cafes, and live music venues - the perfect home base for your Chicago adventure. Extra Fees: *only available upon request and approval* Early Check In@ 2pm : $50 @10am:$100 Late Checkout@ 1pm: $50 @9pm:$100 Shipping: $25 + UPS fees Required for 7+ Days: $80 Cleanin

A spacious living area is displayed, featuring a comfortable brown leather sectional sofa and a glass coffee table. A modern electric fireplace is positioned against a stone accent wall, while natural light fills the room through large windows with white blinds.

Apartment in Oak Park

4.9 out of 5 average rating, 172 reviews

Stunning 2bd 1bath w/free parking, W/D & fireplace

Whether you're here to visit family or friends, to attend a conference in the city or a quick getaway, your family will love renting our entire flat. It has all the comforts of home located on a beautiful block in the historic Frank Lloyd Wright District in Oak Park. Here, you will be close to The Frank Lloyd Wright Home/Studio, downtown Oak Park, amazing restaurants and attractions, the Green and Blue line trains that will take you to downtown Chicago, and major highways and shopping centers.

A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.

Apartment in Oak Park

4.86 out of 5 average rating, 676 reviews

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

A modern kitchen area features a compact island with a sleek sink and metallic fixtures. A round dining table with black-and-white polka dot chairs sits against a light pink floral accent wall. Warm lighting enhances the inviting ambience of the space.

Apartment in Chicago

4.84 out of 5 average rating, 350 reviews

*Entire City Apartment 1 block to Train Park Free

Perfectly private - large & comfortable with full kitchen. FREE & EASY street parking One block to (Green Line) train stop to United Center - Concerts, Bulls & Blackhawk games. Two stops to trendy West Loop Randolph bars, restaurants and shops. 10 minute ride downtown Chicago. Kitchen has cooking utensils & coffee, cream, sugar, spices. Shampoo/conditioner/towels/linens are provided. Free wifi. PLEASE NOTE No visitors No smokers no exceptions and agree per message to confirm reservation

Top guest favorite

A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.

4.98 out of 5 average rating, 159 reviews

Retro Modern Bungalow | fire pit | free parking

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] back yard. 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.

Double French doors open into a bright, inviting living space. A patterned area rug lays on polished hardwood floors, leading to a cozy seating area with upholstered chairs. Decorative artwork adorns the walls, and soft light filters in through the windows.

Apartment in Oak Park

4.94 out of 5 average rating, 180 reviews

A Quiet Stay While You Are Away Oak Park

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

Top guest favorite

The exterior features a charming two-story home with a welcoming front porch. A set of stairs leads to the entrance, surrounded by well-maintained greenery and blooming flowers. Sunlight filters through the trees, creating a warm and inviting atmosphere.

Guest suite in Evanston

4.98 out of 5 average rating, 261 reviews

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!

A wall-mounted shelf displays a selection of games and activities. Notable items include a colorful game box labeled 'Charades', along with stacks of miscellaneous game pieces. Above the shelf, the word 'PLAY' is spelled out using wooden blocks, adding a playful touch to the space.

Townhouse in Chicago

4.88 out of 5 average rating, 371 reviews

CITY CONDO with GARAGE 7 min Walk to Train

Experienced Super-host offers private spacious & sunny condo 3 miles from Chicago "Loop" Lakefront and Museums. Large one bedroom with king size premium mattress, and full sized sofa-bed sleeps 4. 1 FREE garage PARKING wi-fi , washer & dryer. BUS to city center is across the street. 10 minute ride to city center. Walk to United Center Bulls/Blackhawk games /concerts and large international grocery store. Note- WE DO NOT HOST SMOKERS/PERMIT VISITORS. Please agree per message to confirm

A bright bedroom features a spacious bed with crisp white linens, complemented by an abstract wall art piece. A wooden nightstand with a lamp is positioned beside the bed. Large windows provide natural light, showcasing views of the city beyond.

Apartment in Chicago

4.82 out of 5 average rating, 238 reviews

Kasa | Explore the Neighborhood-Mag Mile | 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.

A modern living area showcases tall windows allowing ample natural light. A white sofa is complemented by vibrant red cushions, while a contemporary coffee table sits atop a red accent rug. A dining table for four is visible, and artwork adorns one wall.

Apartment in Chicago

4.88 out of 5 average rating, 249 reviews

1BR South Loop Loft I SuperHost + Top Rated!

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!

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Popular amenities for Cook County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An inviting above-ground pool is surrounded by a wooden deck and protective railing. A ladder leads into the water, and a large white inflatable float is positioned nearby. The area is complemented by green grass and trees in the background, creating a tranquil outdoor setting.

Guesthouse in Merrillville

4.91 out of 5 average rating, 128 reviews

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

Guesthouse in Chicago

4.88 out of 5 average rating, 325 reviews

Private Coach house near Lincoln Square!

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Chicago

4.95 out of 5 average rating, 135 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Pet Fndly

A modern kitchen features a large stainless steel island with seating for three. Black cabinetry offers ample storage space, complemented by open shelves displaying various kitchen items. Pendant lights hang above, illuminating a stylish workspace adorned with greenery, while industrial elements add character.

Loft in Chicago

4.96 out of 5 average rating, 264 reviews

Tea Studio in Wicker Park Spring Factory

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

4.86 out of 5 average rating, 168 reviews

The Spa of Downtown Whiting

Top guest favorite

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Apartment in Chicago

4.98 out of 5 average rating, 134 reviews

Belmont Pleasures - hot tub / arcade gaming room

A dining area is presented with a long glass table set for six, surrounded by tall upholstered chairs. The space features a decorative rug beneath the table and wall art made of natural materials, with soft lighting illuminating the room.

Home in Elmhurst

4.85 out of 5 average rating, 108 reviews

Luxe 3BR, 2BA + Hot Tub

An open and spacious living area features a white sectional sofa and unique cow print coffee table. The dining space is equipped with round chairs, and a modern kitchen is visible in the background. Light streams through frosted glass block windows, enhancing the airy atmosphere.

Apartment in Chicago

4.86 out of 5 average rating, 473 reviews

Checkerboard Studio, Private Outdoor Hot Tub, Yard

Family- and pet-friendly home rentals

Top guest favorite

A collage of the Mini Golf House showcases the vibrant mini golf area, a cozy lounge with arcade games, a comfortable sleeping space, and a living area featuring a large TV. The layout highlights inviting spaces designed for entertainment and relaxation.

Home in Whiting

4.96 out of 5 average rating, 123 reviews

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

A modern living area features a sectional sofa and two armchairs arranged around a central coffee table. Large windows allow natural light to fill the space, while decorative wall art adds visual interest. A flat-screen TV is positioned opposite the seating area.

Apartment in Melrose Park

4.93 out of 5 average rating, 148 reviews

KNG+QN 2bdrm/1parking space /18 min O’hare/Alstate

A cozy living area features a light-colored sofa and a dark armchair, arranged around a wooden coffee table. A textured area rug lies beneath, and soft light is provided by a floor lamp. Large, partially draped windows allow natural light to enter.

Guesthouse in Evanston

4.92 out of 5 average rating, 118 reviews

Cozy Guesthouse near NU - next to Lee Street Beach

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

Condo in Chicago

4.93 out of 5 average rating, 256 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

A two-story apartment building is shown, featuring a light-colored exterior with dual-tone siding. Lush greenery surrounds the structure, including shrubs and grass. A staircase leads to the entrance, while the nearby homes display varying architectural styles.

Apartment in Forest Park

4.84 out of 5 average rating, 308 reviews

Home in Forest Park downstairs.

A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.

Guest suite in Chicago

4.96 out of 5 average rating, 134 reviews

Eddy Street Upstairs Apartment

An open-concept living area features modern wood cabinetry and stainless steel appliances in the kitchen, with a spacious sectional couch facing a large flat-screen TV. Soft beige curtains allow natural light to fill the room, highlighting the warm wood flooring.

Apartment in Chicago

4.9 out of 5 average rating, 133 reviews

Unmatched Urban Retreat Close to 18th Strip & Loop

Top guest favorite

The living area features a wall-mounted TV opposite a light-colored loveseat and a blue armchair. A small round coffee table is situated on a textured gray rug. Natural light enters through the two windows, with modern framed art and a floor lamp adding character.

Guesthouse in Chicago

4.98 out of 5 average rating, 325 reviews

Private coach house near transit shops & nightlife

Family-friendly home rentals with a pool

A living room is displayed featuring a stone fireplace as a focal point. A ceiling fan hangs above a light-colored sofa and a clear coffee table. Dark curtains frame two windows, and a dining table is positioned near the staircase, creating a functional and inviting space.

Home in Schererville

4.92 out of 5 average rating, 64 reviews

Cozy house in Schererville

Condo in Evanston

4.96 out of 5 average rating, 112 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

A modern dining area features a sleek glass table surrounded by curved, upholstered chairs. Floor-to-ceiling windows provide expansive views of the skyline and Lake Michigan. A unique pendant light with a cloud-like design hangs above the table, complementing the bright, airy atmosphere.

Apartment in Chicago

5 out of 5 average rating, 6 reviews

Sky-High Living: Lake Views, Elite Experience

Top guest favorite

A comfortable living area is presented with two soft armchairs and a light-colored couch. A media console houses a Roku TV, while a decorative electric fireplace offers warmth. Artwork adorns the walls, and natural light enters through a window with blue curtains.

Townhouse in Forest Park

5 out of 5 average rating, 11 reviews

Forest Park Oasis - Dog Friendly - Parks - the "L"

Apartment in Warrenville

5 out of 5 average rating, 3 reviews

Luxury 2BR - Pool, Pickleball, Gym, Sauna & More!

An indoor mosaic-tiled pool is surrounded by a spacious, elegantly arched ceiling. Soft lighting reflects off the water, enhancing the serene atmosphere. Wooden lounge chairs are placed along the poolside, providing a comfortable area to relax.

Apartment in Chicago

4.9 out of 5 average rating, 542 reviews

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

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. An island with bar seating is positioned in the foreground, while a spacious archway leads to an elegantly designed hallway featuring artwork and natural light.

Home in Plainfield

4.94 out of 5 average rating, 84 reviews

Beautiful Spanish style Home (w/inground pool)

An outdoor pool is featured with a modern design, surrounded by grey tile and lounge chairs. Clear blue water reflects the sky above. Urban buildings rise in the background, providing a cityscape view from the pool area.

Apartment in Chicago

4.89 out of 5 average rating, 103 reviews

The Executive's Escape (2BD / 2BA)

Destinations to explore