CHILL Yacht Charters is a yacht rental service on Lake Michigan in Chicago, Illinois. Our name itself has the city embedded in it, combining CHI from Chicago, and ILL from Illinois. See what we did there?

Arguably the greatest city in the world from about April-ish to October-ish.  The rest of the year gets a little out of hand with bone-chilling temperatures, snow drifts, all day shoveling, and general misery that takes over your existence. But those warm springs and summers are amazing. The concrete jungle on the waterfront of majestic Lake Michigan, provides a unique environment for Chicago's architecture, culture, culinary, entertainment, and sporting excellence. We look to take advantage of these warm summer months and provide a one of a kind experience to our guests. 

We hope you enjoy visiting our site and will be cruising with us soon, contact us today to set up your trip! 


The heart of our operation lies with Perfect Match, our Cruisers Yachts 4270 Express. Some call her a thoroughbred while others say she has more of a mermaid’s spirit, but however she strikes you we know she’ll leave a lasting impression.


Our lady has a spacious mid-cabin, a stateroom with a private head (that’s boat-speak for toilet) and a stand up changing area. You’ll be surprised by how roomy she is – her interior features tons of storage for your personal items, a small galley for food setup, and a cozy sofa in the lounge area below.

An on-board refrigerator/freezer to keep your drinks cold, microwave/convection oven, and a three-burner electric stove to keep your food warm if needed. A bluetooth stereo system allows you to be the captain of your own playlist. Where our boat really shines (both literally and figuratively) is above board. With plenty of seating and a communal table, Perfect Match’s deck is spacious enough for everyone to enjoy the beautiful Chicago sunshine.