What city has played host to the Legion's national convention the most times?

Chicago. Its years have been 1933, 1939, 1944, 1945, 1958, 1972, 1982 and 1992. Also high on the list: Minneapolis, St. Paul, Minn., Miami and Miami Beach.

You can read The American Legion's recap of the 1933 convention here courtesy of the Legion's Digital Archive; you can also search for the other magazine recaps. The American Legion Library is close to completing its digitization of the entire magazine archive, from 1919 to 2012.

Thanks to the plans for the Legion's Centennial Celebration, convention cities have been set through 2019: Baltimore in 2015, Cincinnati in 2016, Louisville in 2017, Minneapolis in 2018 and Indianapolis in 2019.