House holiday rentals in Cook County

Large Home | Free Parking | Near Downtown

• HUGE Single Family Home | 3 Floors • Parking Garage | 2 Cars! • Chef's Kitchen | Cookware | Utensils • Basement | Two Living Rooms • 4 Bedrooms | 5 Beds | Sleeps 10 • Downtown | McCormick Place: 10min(drive) • Soldier Field | Sox Stadium: 10min(drive) • Chinatown | Pilsen Nightlife: 5min(drive) • Lakefront | Beach | Museums: 10min(drive) • Outdoor Surveillance | Noise Monitoring • Washer | Dryer | Dishwasher in unit (free) • Rideshare(Uber/Lyft) | Bikeshares(Divvy) • Working Class Neighborhood

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

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.

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Chicago Home (1st floor) by Midway near Downtown

Hello, Welcome in 1st floor apt, where 3 rooms are available with newly remodelled kitchen, bathroom and livingroom. LOCATION, convenient location, walking distance to grocery store and few restaurants near by, also walking distance to public transportation bus 62 and 62 H. 5 min driving to Midway airport and 15 min driving to downtown Chicago. Easy access to public transportation to get to Chicago downtown. In addition to convenient location, apt offers access to yard and free parking

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

Feel at home at this cozy split-level ranch with separate spaces perfect for relaxing—whether you’re staying with family or traveling for work. Watch your favorite show in the basement while someone else is peacefully reading a book on the main level or taking a nap upstairs. Located on a quiet, dead-end street, but just 22 mins from O’Hare Airport, minutes from I-290 and 83rd, and 10 minutes from Oak Brook Mall. Our excellent guest-to-bathroom ratio ensures comfort for everyone!

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!

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).

Cozy Schaumburg 5 br/3.5ba w/ bonus rooms/office

Luxurious–Cozy Ranch Stunning 5-bedroom, 3.5-bath home offers spacious modern living on a quiet cul-de-sac. The home features a gourmet kitchen with a Viking 48” stove and Omega cabinets, a master suite with a coffee bar, his-and-hers bathrooms, and a jacuzzi tub. Enjoy two fireplaces, three wet bars, and a basement with a pool table, arcade games, an 85” TV, and a kids' playroom. Outside, the backyard has a patio, gazebo, and firepit.

Modern Aesthetic 3bd Family Haven w/ King Bd, Yard

Unwind in this spacious, family-friendly haven in Elk Grove Village. Featuring a king bed, modern amenities, and a private yard, it’s the perfect spot for a relaxing getaway or a convenient home base to explore the area. The home is centrally located near O'hare Airport and Woodfield Mall, plus it is conveniently located near the intersection of Chicago's two major highways: I-90 and I-290, ready to take you to your destination.

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!