Have you seen the new subway entrances that the CTA is using in the Loop? They're nice. They remind you of the quaint Quincy elevated station (the only CTA station without advertising).
Chicago-L , this entrance is from the mid-80's based on designs from the 70's. It looks like it. Utilitarian in the worst sense of the word. But there's relief just two more blocks away.
Chase Tower (10 South Dearborn) and instead of having layers of caked-on blue paint, it features nice brass plaques and stonework that matches the nearby plaza. Chase finished this project in 2008 and the results are great. Though most people don't think of it, it's a little gift to the city from the bank.