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Book a session (April through October) and head to North Avenue Beach. Strap on your life preserver (or wet suit) and step into the lake for a 30-minute tutorial.
Great Lakes Board Company, 1600 North Lake Shore Drive (773-575-4787 or greatlakesboardcompany.com).
Senior editor Lauren Lumsden embraces her high-maintenance habits. Here are the 27 items she can’t live without — from makeup remover to a smoothie recipe.