This has long been promoted (and still is on the net). The usual candidates are Richard Daley with or without the Chicago Mob. The story goes that the deliver 27 electoral votes to JFK and therefore the election. The problem with this is that Kennedy won the electoral college with 303 votes (269 required to win). So Illinois was not enough to provide the win. One could theorise a Mob assist in Nevada that could have added an extra 3 votes. Without those two states however he still had 273. Johnson on his ticket surely delivered the Texas votes, without that state it would have become more difficult.
Anyone want to debate the topic? Can we put this one to rest? I am not arguing that Daley didn’t push hard for JFK but the notion that Chicago delivers the presidency appears unfounded to me.