"A Christmas Story is set circa 1940, but the Old Man mentions that Ralphie might be able to get a foreign made top at the "Exposition" when it opens.
The Century of Progress Exposition, a.k.a. The Chicago World's Fair, opened on May 27, 1933, when Jean Shepherd was 11 years old. The movie takes place in summer, not spring. The Exposition was also held in 1934.
Like the first film, it's not set in any specific year. There are references that potentially place it in several different years...
This is a rotten way to end it!
This is not the end; you haven't read it yet.
In the Mouth of Madness
This is correct. Some suspect that Jean Shepherd often embellished his tales quite a bit, blending the events that occurred over several years into a single day to make it outrageous. It's possible the years are all jumbled for storytelling effect, leaving people unable to pinpoint an exact timeline.
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