1960 Popular Vote

[Verily]

Since people have 11 different votes, and 318,303 people chose to vote for the most popular Kennedy elector, there does not appear to me to be any reason not to assign all 318,303 votes to Kennedy in the PV. At least 318,303 people wanted him to get at least one electoral vote. Dividing the most popular elector's vote into elevenths is far more absurd; clearly, a large segment of the population wanted Kennedy to get electoral votes, while only around 6,000 voters (assuming a bit of churn) wanted a Democrat but not Kennedy to get EVs. That people did not have the option of voting for more than five Kennedy electors does not mean that they would not have done so given the choice. Nor does the limited nature of the ballot allow us to arbitrarily divvy up the Democratic vote.

As the overall PV was substantially less close than 6,000 votes, the difference is irrelevant.

[Verily]

I heard that Daley got Kennedy elected with dirty machine tactics in Chicago.  Thousands of dead people voted for Kennedy.

Not really, no. Yes, there was massive voter fraud in Illinois, but it happened pretty much equally on both sides. And even had Kennedy lost Illinois, he would have won the Electoral College and the election.