The 1941 work is to hit the auction block Dec. 1. It is the first of Rockwell's series for the Saturday Evening Post that followed the fictional Willie Gillis through his World War II U.S. military service.
"This is an extremely rare and important piece of American history, both culturally and socially," Sean Susanin, co-founder of Susanin's, said in a statement Monday. "We are thrilled it will be sold here in Chicago. It is certainly one of the finest Rockwells, which uniquely demonstrates the artist's unmatched ability to tell a complex story through simple, compelling images."