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The water temps in Lake Michigan are never as pleasant Florida. Even in the best of years we are lucky more than a few dozen days in 70's. Sailing is a lot more practical, there are classes for kids, but because in Lake Forest they are offered by the municipality's Dept. of Parks & Recreation instead of a Park District they have few non-resident slots. That same attitude extends to beach parking, but there are alternatives. LF has a fairly large (by North Shore standards) shopper/commuter lot that is a walkable distance from the beach...
Glencoe has a really nice set-up, with a modern egalitarian concession area, showers, playground, though parking is similarly restrictive.
Not sure that any town really rents chairs...
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