Were there any Chicago bound PRR trains departing N.Y. Penn Station before noon, circa 1950? If not, did Penn Station serve any other roads besides the Long Island and the New Haven during that period?
Jerry, the Boston & Maine, in partnership with the New Haven and Pennsylvania ran at least one train during the summer months during the late 40's and early 50's. As I remember, it ran weekly between Washington and the New Hampshire mountains. The train I'm thinking of left Washington around noon on Fridays, was split into two trains at Ayer, MA, and arrived in northern NH sometime Saturday morning. The return trains left NH Sunday afternoon, rejoined at Ayer, and arrived in Washington mid-morning Monday. I'll research more information on this and other B&M trains that may have terminated at or run through New York's Penn Station.
I also found that the Pennsylvania, New Haven, and B&M ran the East Wind between Washington and Portland, ME during the summers of 1940-1942. The East Wind was an all coach with a buffet/lounge train that carried northbound passengers for only Worcester, MA and north. Furthermore it ran daily except Saturdays. The train I referred to in my previous post carried sleepers, possibly with coaches also, though I can't confirm that.
Have you checked Jerry Britton's website? It's a wealth of information on all things Pennsy. Here's a timetable from 1954 (NY to Chicago service is on page 12). http://kc.pennsyrr.com/passops/downloads/ptt_540926_form1.pdf Looks like the earliest NY to Chicago train is the Manhattan Limited leaving NY at 2:45 PM. The major problem is that if you leave New York in the morning, you will arrive in Chicago very late at night, if not the wee hours of the next morning. Here's a link to Jerry's Passenger Operations page, which might have something that I missed. http://kc.pennsyrr.com/passops/index.php In response to the second part of your question, it looks like the Lehigh Valley also used Penn Station.