Chicago doesn't seem to have any pirates today that I can find.
Going back 20 years, I was 100 watts on 7.415 Mhz with the same format I now run 100mw on 1620 AM.
Difficult music. Oldies/20's-30's swing/jazz/new alternatives that sounds like mid 60's psychedelic/doo-wop/eclectic/texas swing/TV themes/old commercial spots/gospel/punk/thrash/bluegrass, psychobilly/garage rock/ska/comedy audio clips/etc.
It is interesting to note when I listen to old airchecks of the pirate days, how much my vision is true over the last 25 years.
A playing of a cassette mix tape I made in 1985 might easily drop into my playlist with no notice except for no songs newer than
the date of recording. I play a good deal of new music now, but the casual listener might think they are old recordings.
King Khan (with or without BBQ) is a great example of new rock that doesn't care about years and time.
It's NOW, but could be from any year 1960-forward and as grungy as Link Wray in his gnashiest moment.
The vocals are a cross between Bo Diddley and Andre Williams singing "Agile, Mobile and Hostile".
Y'know, just regular music. Except what you can hear everywhere else.
Back then I was nationwide, and paid a fine for all the fun I had.
Today I go 3-4 blocks and am very happy that thousands of people live in that tiny circle.