Metra, which runs Chicago's heavy-rail commuter lines, hasn't changed much at all since the 1970s, as today's Chicago Tribune describes in sad detail:
Metra runs on paper, as in paper tickets. Although the majority of riders use monthly passes, passengers in January still bought more than 666,000 one-way tickets or used 10-ride tickets, which conductors have to punch individually.
... Other open rail systems have done away with punching and checking individual tickets. For example, conductors on Boston's Massachusetts Bay Transportation Authority check tickets with hand-held electronic devices. ... On Caltrain, a commuter rail line operating between San Francisco and San Jose, passengers buy tickets from vending machines and conductors make random checks. Anyone without a ticket faces a $250 fine.
[And] it's cash or checks only on Metra. The line doesn't take plastic because of the processing fees that credit-card companies impose, Metra spokeswoman Judy Pardonnet said.
The article also mentions a lack of information about train whereabouts that even our CTA buses provide.
I think the article makes Metra sound better than it really is, simply by comparing it only to its American analogues. The authors ignore, presumably out of pity for Metra, the Shanghai Maglev at one extreme, or even more typical European rail systems like Berlin's S-Bahn and the UK's Oyster Card scheme as examples of how to modernize at the very least how people pay for transit.
All right, maybe Transport for London isn't the best example. Still, when Boston has free Wi-Fi and we can't even pay with credit cards, something is wrong. At least TfL has a dedicated express train running from Heathrow to central London (on which you can use your Oyster Card), and we have...the Blue Line. Sad, really.