Are you staying overnight? If so where?
I had a lot of experience - business related - staying overnight in Chicago all through the 1980s-19990s and had a couple leisure stays there in very early 2000s. The experience then was not unpleasant. But then again my visit included nothing below the very downtown core, nothing above Lincoln Park and more on the east (lake) side than the west side, with a few exceptions.
I’ll be on around Chestnut and Rush street.