Not to mention the fact that the guy at IIT and the Lakeview-to-suburbs guy could shorten their commutes significantly by throwing a bike into the mix.
My sister lives in Humboldt Park and works in Arlington Heights. She moved here a couple of years ago from Louisville, Ky., where she was car-dependent. She got her apartment before she got her job, so she couldn't pick a place that was close to the right public transportation option. On job day one she started biking to the Metra, putting her bike on the train, then riding from the station the couple of miles to her office. It has worked out pretty well. She bought a cheap beater that she can leave out there for the bikes-on-trains blackout dates.
I'm always amazed that someone would be willing to spend hours on the bus when bicycling often is a viable faster alternative. But to each his own!