Holiday rentals in Cook County

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Little Gem Double Rm Home Base for Chicago Trips!

Great home base for Chicago adventures & PREMIUM location in the epicenter of Oak Park - America's home of prairie architecture! Beautiful park/Frank Lloyd Wright homes are directly outside your door and you are only a 25-minute train ride to Millennium Park & all of Chicago! Eclectic garden level (shared) apartment decorated with fun and funky furnishings. Private Bedroom with new double size bed, deluxe bedding, towels. Shared bathroom, living room, and kitchenette. View my other 2 listings!

Charming Chicago suburb! 1 bedroom apartment.

Enjoy your stay just west of Chicago in our 1880 updated 1st floor of a 2 flat. You get a one bedroom apartment with queen bed, private kitchen and bath, separate office for work, plus 2 porches for you to enjoy. Brookfield is a charming village with unique restaurants, bars, salon and day spa, coffee shops, library and the train to Chicago--all within a 5 minute walk. We want you to feel at home; but before you book understand that you may not smoke ANYTHING in the unit or on the property.

The Albany Park Room at the Cape Cod in Riverside

The Cape Cod in Riverside is 10 miles from downtown Chicago, accessible via METRA and CTA Blue Line. It's a block from a trail entrance, a mile from Brookfield Zoo, and close to Riverside's historic downtown and Loyola University Medical Center. O'Hare Airport is 18 miles away, and Midway is 9 miles. The Albany Park Room, one of two Airbnb listings, is on the second floor and accommodates two guests. The property supports sustainability with partial solar energy for heat and hot water.

2B Midcentury Artist Loft w King Bed

Welcome to Casa D'Mi Amá, this vibrant mid-century loft style apartment is centrally located in Little Village, one of the most vibrant Mexican-American communities and thriving shopping district in Chicago. Our community is known for its colorful murals and hundreds of Latinx-owned businesses and restaurants. We are just 4 mile away from downtown & Midway airport, three miles away from Pilsen & UIC, with public transportation right outside your door making it easy to plan your visit.

Sonder Market Hall | King Studio Apartment

Overlooking Union Park, Market Hall is the perfect blend of city and seclusion. You’ll have leafy green views, paved walking trails, and endless global cuisine options on Randolph Street. Each room includes a fully equipped kitchen, in-suite laundry, and a Roku for streaming. And take advantage of the free weights or machines in the fitness center. The West Loop is a trendy hot spot for foodies and entertainment seekers. Enjoy the best of the Windy City at Market Hall.

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Urbal retreat

On the cusp of urban and rural, urbal. To the north, the sprawling and windy city of Chicago. To the south, farmland and more open spaces. Small bedroom in a nice house on a quiet street. Living space shared with me, my boyfriend, Dillon and my 10 year old son and dog Chase. Walking distance from the train to downtown Chicago. 5 min drive to highway and area with shopping and restaurants.

Cozy Guest Suite. Private Entry+ Turo Rental

3600 sqf single family home with a Guest Apartment and private entry on the ground level. Your family will be close to everything when you stay at this centrally-located place. Centrally located off of I294, I55, I57 and I80. Easy to and from travel. In Need of a rental we have 2018 Jeep Grand Cherokee High Altitude at the house and listed Turo.