Chicago Cruises: from Summer to Fall

By September 23, 2020Uncategorized

Chicago has always been known for its wild weather, and this summer was no exception. The city had the driest stretch since 1944 and it was also the hottest summer ever recorded in Chicago, ensuring that 2020 will go down in Chicago history.

When the weather is hot and dry, Free Spirit has you covered! Our Free Spirit and Gypsy Spirit yachts will take you out far enough on Lake Michigan so you feel the summer breeze and enjoy the magnificent views of Chicago.

As the fall season approaches, locals confirm that it is one of the best times to visit Chicago. Lake Michigan cools down slowly, keeping the shores warmer. For some, September and October are arguable the perfect months for a cruise!

Not to mention, the fall foliage is beautiful throughout Chicago, and from the deck of our Free Spirit yachts, the views are even better! The colors of fall lining Lake Michigan provide a perfect background for group photos to remember your cruise experience.

We’ve gotten joyful feedback from our charter clients that cruised during the fall season:

“Great Yacht moonlight cruise last night! Thank you captain for a beautiful night!”

“I always thought it would be fun to have my company’s employee appreciation day chartering a yacht on Lake Michigan. Well my expectations were far surpassed. Joe and Angela have two beautiful boats, depending on the size of your outing. The food and drinks were outstanding. We even deviated slightly from the menu without a problem. The price was fair and the service spectacular. All employees were blown away by the experience. I would highly recommend Free Spirit Yacht Cruises.”


We spend a lot of time each season sending out pre-charter emails to reassure clients who are concerned about the weather. We monitor weather radar conditions very carefully, and our captains and crews are highly experienced. They’ve all been out on Lake Michigan when the weather suddenly turned from sunny and beautiful to dark and stormy or heavy with fog.

When unfortunate weather happens, we’re always prepared and never cancel charters. You’ve already invited guests. The food’s been ordered. Our yachts are large enough to have your group inside (where it’s cozy and heated). If the weather is very threatening, we will stay in the harbor. Otherwise, we cruise!

Click here to book your cruise today!

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