"Vote Early. Vote Often." Old standing joke for election day in Chicago.
John Kennedy beat Richard Nixon in 1960 with the help of suspected fraud in Illinois and Texas. Among the documented cases of ballot stuffing in that close election was a precinct in Texas's Angelina County where only 86 people voted. Yet the final count was 147 for Kennedy and 24 for Nixon. Fannin County, Texas, had 4,895 registered voters, but somehow they cast 6,138 votes, with three quarters for Kennedy. And there is strong evidence that the Daley machine in Chicago was responsible for Kennedy winning Illinois by 8,858 votes. Kennedy received 456,312 more votes than Nixon in Chicago, whose precincts reported their totals remarkably late. (Kennedy's nationwide victory margin was only 118,574 votes.) Voter turnout in the Daley-controlled precincts was a spectacular 89 percent compared with the nationwide turnout of 63 percent.
Chicago gave Illinois to Kennedy. Illinois gave Kennedy enough electoral college votes to go over the top. And before you say this is Urban Legend...
File this under "Don't Make No Waves, Don't Back No Losers."
Ultimately, a special prosecutor, Morris Wexler, was appointed to investigate the Chicago fraud allegations. Wexler brought charges against 650 election officials but a Democratic judge's pro-defense rulings crippled Wexler's case and the charges were dropped.
Finally, in 1962, after an election judge confessed to witnessing vote tampering in Chicago's 28th ward, three precinct workers pled guilty and served short jail terms.
A new biography, "American Pharaoh," quotes Mayor Daley defending his city by claiming that Democratic fraud in Chicago was no worse than Republican fraud in downstate Illinois:2 wrongs = 1 right?
More recent allegations of Vote Fraud exist in Chicago, though none in 2008.
At this point, I could segue into why Kennedy was assassinated, but I think you know my theories already. (The most unforgivable sin = disloyalty. 1st act as Pres? Appoint Bobby AG, and start in on organized crime.)