2.72 million people in Chicago, so if he does like maybe 20 a day that's 68,000 days, which is about 186.17 years.
Hmmm, that's not going to work. How old is he now? To do it in 60 years means having *** with about 60 people a day. Assuming you'd even have that long, since if the fatigue doesn't get you I'd think some kind of STD, and more likely many kinds of STDs, would find you. Not to mention who really wants to have *** with a 80 year old man who's slept with 2.7 million other people. The luster would fade eventually. Would need to be done a lot quicker than that...
Even a quick, pop-it-in then pop-it-out, would take what, maybe 15 seconds per person if we're trying to be efficient here. 4 per minute * 60 minutes * 16 hours a day would be 3,840 people a day. That would take you almost 709 days, or nearly 2 years. That's probably doable before you die from some disease, wear and tear is a whole different concern of course.
That monster in the mirror, he just might be you. -Grover