Family-friendly holiday rentals in Des Plains

A spacious kitchen area is shown with modern stainless steel appliances and ample cabinet storage. A large wooden dining table is centered, set with decorative placemats. Soft light illuminates the room, complementing the neutral color scheme of the walls and cabinetry.

4.97 out of 5 average rating, 118 reviews

Newly remodeled O’hare oasis

Your family will be close to everything when you stay at this centrally-located place. This 3 bed 2 bath newly remodeled private home will have everything you need to feel comfortable during your stay! You are 3 miles from O’Hare airport ,2 miles from Rivers Casino, 1 mile from Allstate Arena, and 4 miles from Fashion outlet mall of Chicago. Enjoy spacious living room and Rec Room, large eat-in kitchen with all new appliances! King bed . 2 queen Beds and pullout sofa with queen bed for sleeping

An open living and dining area features a large table set for meals, surrounded by comfortable chairs. A cozy sectional sofa sits nearby, complemented by a ceiling fan and a wall-mounted TV. Natural light flows in from windowed areas towards the rear.

4.85 out of 5 average rating, 165 reviews

Entire house, close to O'Hare airport

You and your family will be close to all amenities when you stay at this centrally-located place. 5 miles from O'hare Airport, 1.3 miles from Allstate Arena, 4 miles from Rosemont Convention Center and 5 miles from Fashion Outlet of Chicago. Few mins from Rivers Casino, Shopping Centers, Restaurants, Express way. Easy access to I-90 & I-294. 15 miles away from Chicago Downtown. A newly renovated space with extremely fast WIFI up to 800mbps, suitable for WFH. Walking distance to a close by lake.

4.94 out of 5 average rating, 885 reviews

A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.

Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot/cool tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

4.76 out of 5 average rating, 628 reviews

A modern kitchen area features a wooden accent bar with four metal stools. Stainless steel appliances, including a refrigerator and stove, are visible. A wall clock adds a functional element to the open concept design, with neutral tones enhancing the spacious ambiance.

Flat in Park Ridge

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level garden apartment one bedroom one bath. Older building with wooden floors. If hearing people upstairs walking can bother you , do NOT book it please .Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10min to outlets Absolutely NO parties, NO gathering Quiet hours 10 pm till 6.00 am

Guest suite in Riverwoods

A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.

4.95 out of 5 average rating, 493 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

The spacious family room features a high vaulted ceiling with exposed wooden beams. A stone fireplace provides a central focal point, and a large TV is mounted above it. Comfortable seating is arranged for relaxation, complemented by a stylish area rug.

4.97 out of 5 average rating, 129 reviews

NEW~2 Spa Baths~Game Room~Prime Area~Big Yard~

✅Updated Home- RARE 1/3+ Acre Fenced Yard 🏠 ✅Huge Vaulted Ceiling Family Room 🛋️ ✅2 Full Updated Bathrooms on Main Level🪥🛀 ✅Game Room w/Air Hockey & Basketball🏒🏀 ✅Dining Room Seats 10🪑 🍽️ ✅Quiet Neighborhood + Convenient Location🏘️ ✅Open Kitchen Floorplan 🍳👨‍🍳 ✅Outdoor Seating🌳 ✅EZ Driveway Parking for 4 Cars🚗🏎️ ✅Close to O’Hare Airport(8 Min)🛫 ✅Close to Stephens Convention Center(12 Min)👨‍👩‍👧‍👧 ✅Close to Allstate Arena(7 Min)🎤 ✅Close to River’s Casino(8 Min)♥️🎰

4.95 out of 5 average rating, 133 reviews

A sleek wall-mounted television is set above a modern electric fireplace, framed by a stylish metallic trim. The stone feature wall provides a textured backdrop, while warm wood flooring complements the contemporary design.

Townhouse in Des Plains

Upscale 3 bed 1.5 bath near Chicago O'Hare Airport

Free! coffee station with 12 types of Keurig pods such as Dunkin/Starbucks/McDonalds/Green tea/Decaf etc. Make your favorite coffee on our commercial brewer. Newly remodeled, luxurious, 3 bedrooms, 1.5 bathrooms duplex house located 10 minutes from O’Hare International Airport. 10-15 minutes from Allstate Arena, Rosemont Convention Center, Fashion Outlets of Chicago and Rivers Casino. Downtown Chicago is ~25 minutes away with an easy access to I-94 and I-294 Expressways

The exterior of a two-story home is depicted, featuring a combination of white and black siding. A prominent bay window enhances the facade, while landscaped flower beds with red mulch and small plants frame the entrance. Green grass and a sidewalk lead up to the house.

4.9 out of 5 average rating, 176 reviews

Cozy Home by O'Hare + EV Plug

Family-friendly 3BR/2BA home in Des Plaines! Enjoy arcade games, board games, and an EV charger. Nestled in a quiet neighborhood near parks, shopping, and entertainment. Just minutes from Des Plaines Theatre, Rivers Casino, Mystic Waters, and Fashion Outlets of Chicago. Ideal for families or groups seeking comfort, fun, and convenience with easy access to top attractions and O'Hare Airport. Your perfect home base for exploring the Chicago area!

4.84 out of 5 average rating, 128 reviews

A bright sleeping area features a black metal bed dressed with a yellow quilt and accented by a green decorative pillow. A light blue sofa sits nearby, complementing the space. Natural light filters through the window, partially covered by blue curtains.

Flat in Des Plains

Safe, Great Location 2 Bedroom Apt, Self Check-In

This gorgeous second-floor apartment is located only 10 minutes from O'Hare International Airport. Located near Des Plaines River Road and Toughy Ave., you will be close to not only the airport but 7 minutes to Rivers Casino, 10 minutes from the Rosemont Entertainment District, and 30 minutes from downtown Chicago. The apartment is minutes away from two major highway interstates, which makes this a commuters ideal location.

4.99 out of 5 average rating, 150 reviews

A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.

Home in Lombard

Modern Boho house in Lombard 7 min to Metra

Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

4.83 out of 5 average rating, 106 reviews

Cozy Home near O'Hare & fun Hubs

Relax with the whole family at this peaceful place to stay. Experience comfort and convenience at our newly remodeled cozy house, perfectly situated near O'Hare Airport, Allstate Arena, and Rosemont Theater. Ideal for travelers and entertainment enthusiasts, this charming Airbnb offers modern amenities and a warm ambiance, ensuring a delightful stay. Book now and enjoy the best of Rosemont!

4.96 out of 5 average rating, 163 reviews

A bright living area features a plush green sofa and a glass coffee table, set against light-colored walls. Near large windows, a small dining table is complemented by four chairs. Natural light fills the space, creating a welcoming and airy environment.

Home in Norwood Park

3BD Home Mins from Airport | Free Wi-Fi + Parking

Cozy home near O'Hare airport with a huge park just behind the backyard, located in one of the safest neighborhoods in the City of Chicago. Quick access to the expressway and short walk to the CTA Blue Line train/bus station. Conveniently located within 5 miles of: - O'Hare Airport - Rosemont/Donald E. Stephens Convention Center - All-State Arena - Fashion Outlets of Chicago

Popular amenities for Des Plains family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 128 reviews

Home in Carol Stream

Lake Home Retreat! HotTub• FirePit• Kayak• Fishing

4.88 out of 5 average rating, 388 reviews

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.

Guest house in Chicago

Private Coach house near Lincoln Square!

4.87 out of 5 average rating, 133 reviews

A spacious outdoor deck is covered with a bright shade sail, providing relief from the sun. Comfortable wicker chairs with soft cushions create a cozy seating area, overlooking the peaceful river and surrounding greenery.

Home in Algonquin

The River House Sauna/Kayaks/Hot Tub/Fire Pit

4.91 out of 5 average rating, 130 reviews

Home in Montgomery

Skip the hotel! Relax here!

4.88 out of 5 average rating, 101 reviews

A spacious living room features a rich blue accent wall and mid-century modern furniture. Two armchairs and a plush sofa are arranged around a low coffee table. A television is mounted on the wall, complemented by decorative wall art. Natural light fills the room.

Home in Westchester

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

Apartment in Little Italy

A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.

4.94 out of 5 average rating, 278 reviews

Private hot tub - King bed suite - Free parking

4.86 out of 5 average rating, 107 reviews

A spacious living room features comfortable seating on soft gray furniture, including a large chaise and armchairs. Natural light brightens the area, while a gas fireplace is set within a stylish stone surround. A large flat-screen TV is mounted above the fireplace.

Home in Lake View

Entire house in Lakeview with yard and garage

4.96 out of 5 average rating, 303 reviews

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 Wicker Park

Tea Studio in Wicker Park Spring Factory

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 147 reviews

A well-lit bedroom is presented with a spacious bed adorned with a light-colored quilt. Two bedside lamps illuminate the area, and decorative artwork featuring coastal themes is displayed above the headboard. A window provides natural light, framed by neutral curtains.

Flat in Glenview

Cute little 2BR near ORD.Clean quiet. No clean fee

Townhouse in Hoffman Estates

A cozy living area features a black leather sofa paired with decorative pillows. A glass coffee table sits atop a patterned rug, complemented by a lamp and a small plant. The staircase leads to an upper level, with a wall map artwork enhancing the space.

4.89 out of 5 average rating, 389 reviews

a SIMPLE place

4.77 out of 5 average rating, 150 reviews

A spacious living area features an array of seating options, including a light gray sofa and colorful accent chairs. Natural light floods in through multiple windows, highlighting the wood flooring and inviting decor. A dining table is situated nearby, along with a small coffee station.

Home in Elmhurst

Cozy Ranch w/ King Bed & 3 Baths – Great Location!

4.95 out of 5 average rating, 247 reviews

A light-filled dining area features a wooden table surrounded by four chairs. A plush sofa is positioned nearby, offering a cozy option for relaxation. Large windows dressed in navy curtains provide a view of the outside, contributing to an open and inviting feel.

Flat in Jefferson Park

Entire 1st Floor Apt near O'Hare/ORD & Blue Line

4.89 out of 5 average rating, 115 reviews

A living area is presented with a comfortable gray sofa adorned with decorative pillows. Two white chairs with blue accents are positioned nearby. Natural light enters through a large window, complemented by dark blue curtains. A patterned rug enhances the inviting ambiance.

Home in Wood Dale

King bed, dog friendly, right by O'hare airport!

Guest suite in Highland Park

4.78 out of 5 average rating, 193 reviews

Your relaxing stay in Highland Park

4.94 out of 5 average rating, 178 reviews

A cozy living room features a pair of light-colored sofas and an accent chair, positioned around a rustic coffee table. A patterned area rug lies underfoot, while a mirror with a wooden frame and wall art enhance the space. A partial view of the kitchenette is visible in the background.

Home in Highland Park

Cozy 2-Bedroom Cottage Near Downtown Highland Park

4.87 out of 5 average rating, 242 reviews

A stylish living area features a comfortable blue couch adorned with decorative pillows. A glass coffee table sits atop an area rug, surrounded by an array of colorful artwork on the walls. A cozy sleeping area is visible in the background, draped with vibrant blankets.

Home in Evanston

SW Evanston Private, Stylish, Spacious Suite

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 138 reviews

An open-concept living area features large windows that invite natural light and provide a view of the cityscape. A comfortable blue sofa is adorned with patterned pillows, while a light wood coffee table sits in front of it. A dining space with black chairs complements the modern kitchen.

Apartment in Evanston

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

Guest suite in St. Charles

A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.

5.0 out of 5 average rating, 322 reviews

Peaceful Private Coach-House in St. Charles

4.98 out of 5 average rating, 163 reviews

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

Flat in Logan Square

Fun & cozy getaway w/POOL/game room/FREE parking

4.9 out of 5 average rating, 597 reviews

A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.

Flat in Uptown

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

4.96 out of 5 average rating, 236 reviews

A red sofa is positioned in front of a brick fireplace, creating a cozy seating area. A wooden coffee table is placed in front of the sofa. Soft lighting is cast from a lamp beside the sofa, and framed photographs adorn the walls.

Guest suite in Bartlett

Cozy & Spacious Suite in Quiet Neighborhood

4.82 out of 5 average rating, 348 reviews

A bright living area features large windows that offer city views, enhanced by natural light. Comfortable gray seating is arranged on a patterned rug, complemented by modern decor and greenery. A flat-screen TV is mounted on the wall, alongside a stylish coffee table.

Flat in Chicago Loop

Spectacular 2BR Penthouse in the Loop | Roof Deck

4.9 out of 5 average rating, 138 reviews

An outdoor pool is surrounded by lounge chairs in various colors, creating a bright and inviting atmosphere. Tall buildings are visible in the background, and the pool reflects the clear blue sky overhead.

Flat in Downtown Chicago

The Executive's Escape (Fitness Center • Sauna)