Windy City Haven
5 guests
2 bedrooms
West Loop, Chicago
Welcome to a distinguished spot nestled in the vibrant pulse of the West Loop! All visitors are skillfully screened for safety and a damage hold is acquired prior to stay.
Cook County Weekend House Rentals
We selected the 85 homes worth renting in this location
Home spotlights in Cook County
Loop Luxe
5 guests
2 bedrooms
Chicago Loop, Chicago
Welcome to the heart of Chicago's vibrant Loop district, where the ultimate urban oasis awaits. Step into Loop Luxe and experience the perfect blend of style and comfort.
Lost in a Moment
6 guests
3 bedrooms
Chicago Loop, Chicago
This pad right in Chicago's South Loop puts the city at your fingertips. While foodies chow down at the many delicious restaurants on your doorstep, culture vultures can spend the afternoon roaming around the famous Field Museum and other nearby galleries.
We selected the top 3% holiday homes in Cook County Weekend House Rentals
Explore the 85 most perfect homes in our collection
View on map
Popular in Cook County
Check upcoming rates & availability for Cook County Weekend House Rentals
Frequently asked questions
Looking to book a holiday rental for the weekend in Cook County, Illinois, United States? You've come to the right place: we’re the official selection of the world’s best homes. Our collection of weekend rentals in Cook County, Illinois, United States come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. We obsessively check each home for you, so you can book with peace of mind. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
Search Our Collection