Did that Chicago album have a history of reviewers saying the engineering was "off" or the recording "flat"? I think any particular album (or any recording, really) could suffer from the original way it was engineered, but like the others have said, the condition of your particular vinyl may be to blame.
One old original from "back in the day", Black Sabbath's Paranoid, the song Paranoid, has always sounded to me like someone made a mistake and had the controls set wrong when the tapes were made. The guitar solo sounds muddied and awful, definitely NOT showcasing Tony Iomi's talent. I love the band and the song, but cringe every time I hear the solo.
Interesting topic. I have hundreds of old discs I have collected from back when I was a teen, and I always made an attempt to use a Discwasher most times I spun them, which had to be thousands of times for some of them by now. I can't say that any have degraded sound from playing, other than the delightful pops and tics that are inevitable with that many spins and 5 years of college beer parties.