Slice of Life: Chicago’s Sailboats Begin Their Annual Procession to Lake Michigan

A sailboat is a hole in the water, into which one throws money.

The happiest two days of a sailboat owners life are the day he buys the boat and the day he sells it.

I know most of the wry observations of sailboat owners, as a recovering one myself. It’s hard to deny the calm you feel as the wind whooshes through the sails.

Ah, but getting a sailboat to a body of water, that takes a little doing. For Chicagoans, it often means getting the boat from winter drydock to a berth on Lake Michigan. The mast of modest size sailboats can approach 50-60 feet tall. So navigating the Chicago River for a sailboats means waiting for the bridges to lift. That occurs in the spring on Wednesday and Saturday mornings.

Since traveling by sailboat is not a speedy affair, Chicago sailors use the time waiting for bridges to lift to basically do nothing. I never said sailors were normal.

The spring bridge-lift does offer some interesting visuals along the river, with the boats in the foreground and the cityscape behind it, as these photographs show, taken May 10 between Washington Street and Wolf Point.

Author: Bill Motchan

Bill Motchan is a writer and photographer, and a former resident of the West Loop. He can be reached at

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