As a person who takes public transportation on a regular basis, from one end of town to another, I've actually seen plenty of improvements to the CTA bus and train system over the last fifteen years or so. The addition of screens with real-time announcements of when the next buses or trains should be arriving is a major plus, as is the ability to access this same information online through the Bus Tracker and Train Tracker features. Most of the time these predictions are fairly accurate, making it easier to plan your trip. for example, they help you decide when to leave your home in order to minimize your wait at the bus stop or 'L' platform, meaning less time out in the heat, rain, or snow.
However, if I was running the CTA, one thing I definitely would change would be to add 24-hour service to bus lines where it is needed. For example, I live in Chatham and the 87th Street bus is the closest route for me to take to and from the Red Line. In the past the #87 ran all night, but in recent years the overnight service was cut. So if I'm coming home from the Red Line late at night, I have to ride the 79th Street bus, which means a longer walk from the bus to my house.
Now, it certainly makes sense for the #79 to offer around-the-clock service, because it's the busiest bus route in the system, with an average of 24,300 boardings per weekday in 2017. But the 87th Street bus is nothing to sneeze at either, with 11,838 boardings per weekday on average, so it seems like 24-hour service would make sense on that line as well. It would certainly be more convenient for us Chatham residents who live further south.
Another pet peeve of mine is the Ventra card. This has to be the most cumbersome fare payment method ever devised. If you're going to be riding a bus and want to know how much money is left on your card and add value if necessary, you have to stop beforehand at a Ventra retailer, like a currency exchange or a drugstore.
And while 'L' stations have Ventra machines, they take an ungodly amount of time to recharging your card. Several times I've approached a Ventra machine, only to find that the previous user didn't finish their transaction. They may have gotten their card recharged, but likely no one had time to wait around for the receipt. It would have only taken a few seconds, but you don't have a few seconds to spare when your mind is on catching the next train. And, heck, at least with the CTA's old magnetic strip Chicago Card, you got a reading of how much money was left on your card right at the turnstile -- Ventra doesn't even do that.
Those grumbles aside, it's good to live on a city where, depending on you live, it's fairly easy to get where you need to go using public transportation. But, of course, there's definitely room for improvement.