Metropolis Respite
7 guests
3 bedrooms
Fulton River District, Chicago
Welcome to The Willis! To ensure safety, all guests must pass our screening process and provide proper ID.
Chicago Homes for a Watersports Holiday
We selected the 36 homes worth renting in this location
Home spotlights in Chicago
Chicago Morning
8 guests
4 bedrooms
Printer's Row, Chicago
Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.
We selected the top 3% holiday homes in Chicago Homes for a Watersports Holiday
Explore the 36 most perfect homes in our collection
View on map
Check upcoming rates & availability for Chicago Homes for a Watersports Holiday
Frequently asked questions
Find the best homes for a watersports holiday in Chicago, Cook County, Illinois, United States. Every one of our properties has been meticulously vetted by our Plum Guide experts, so you don't have to worry about anything, from the WiFi speed to water pressure. All of our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Arrange your getaway today, and stay in one of the best homes for a watersports holiday in Chicago, Cook County, Illinois, United States.
Search Our Collection