Well, you can certainly tell from reading the posts here who's a frequent flyer and who is not. "Buddah", when did you last fly? I haven't seen a 727 in passenger service in more than a decade (a few still fly for the package express firms). And, unless you're taking an international flight, you certainly don't need to be at the airport, clear of security and checked in, two hours before a flight. I generally give it an hour or maybe a bit more at peak times. So your time comparisons for a Chicago -- Toronto trip are bogus. Anyway, why don't you fly from Midway? It's a LOT closer to the Loop.
Post 9/11 security has added some time, but except in the Northeast Corridor, it's almost always faster to fly than take a train. Even in the NEC, when you add on the time to get to and from the station, the train is roughly time-competitive with driving. Example: NY to WAS, a trip I do about twice a month. My wife drives me to 30th Street in the morning on her way to work. Generally we leave the house at 6 AM for an 0655 train. Train takes about 1:35, arriving New Carrolton at 0830 (unless we get stuck behind a late MARC train, as happens about every other trip). I can generally be in the office by 9 AM. Elapsed time door to door: three hours. If I drive, I usually use Delaware Route 1 and US 301, then US 50 from Annapolis into DC. Elapsed time: reliably three hours, a bit less if I get lucky with traffic and lights.
Return trip is similar. I leave work at 1600 for a 1705 train that arrives PHL at 1855 (and, about one trip in two, is five minutes or more late). I'm generally home by about 1930. Elapsed time: three and a half hours. Driving is quicker.
And driving is cheaper, too. And on that subject...one reason I took trains so infrequently during all those years of consulting was that, generally, air travel was cheaper than overnight trains (with sleeping accommodations). Example: PHL to Jacksonville, FL, a trip I used to make several times a year. Typically air fare, plus one night in a hotel, plus transportation to and from the airport in Jax, was at least a couple of hundred dollars less than Amtrak wanted for round-trip roomette accommodations -- and in Jax, the train station is farther from downtown than the airport. And of course, if I took the train I'd be away from home for two nights, versus only one if I flew. And frankly, the Omni Jacksonville is quite a bit more comfortable than an Amtrak roomette.
So, outside the NEC (and a few spots on the West Coast) Amtrak is really out of the question for business travel.
Randy Resor, aka "NellieBly" passed away on November 1, 2013. We honor his memory and his devotion to railroading at railroad.net.