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Best time to visit Chicago

Sailing Season in Chicago 2025

Sailing is much time limited in Chicago due to the weather conditions

Best time: May–October

Lake Michigan is the second largest Great Lake with diverse beautiful landscapes to explore. The lake is bordered by the states of Michigan, Indiana, Illinois and Wisconsin. Its vast coastline includes not just the fabulous waterfront of Chicago, but also picturesque Milwaukee, the Michigan sand dunes, or the Beaver Islands. Green Bay on the west side is also hope to some small islands, called "the death's door" due to the number of ships that crushed here. However now the Door County today is a great spot for sailing!

Sailing on Lake Michigan is safe up to six month, from late spring through early autumn. There are quite a few rentals available, so you can easily arrange a nice brisk sail!

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