When I was at NIU, I used to listen to, at the very end of it's day, the old 103.9 WABT- The "Wabbit" from Dundee, transmitter still in Gilberts at the ball field next to the tracks. Those guys had a LOT of fun there!
Also...WDEK-FM 92.5 DeKalb, when it was local. DJ's 24 hours a day back in the early-mid 1990s. They played "CD sides" of Top 40 groups all night long. Talk about depth! I remember when they were giving away free pizza from a pizza place long moved just north of the station back in 1991. From 5-6 PM, just come and grab a few slices. MANY HUNDREDS showed up. For DeKalb, that was a huge promo turnout!
WJOB-AM 1230: live, local 24/7, when a tornado warning happened at 2 AM, they were there and on it. Larry Peterson had an amazing voice, I'd tune in just to hear him.
WKAN-AM 1320 was just as good and played A/C all day...wide variety. In Calumet City, I could get them, and it was a treat to listen to them.
WLLI-FM 96.7 "I Rock"...wow. If you liked rock, it was the place to rock.
WBUS "The Bus" 99.9 FM...Chip St. James and others rocked the place. They always rated a .3 to a .6, fer crying out loud. That's HUGE for stick on 57 next to Peotone! It was done from a house.....literally, a house!
And remember when you could be the 10th caller and win tickets? Yeah, they were always lawn seats, but the suburban stations had 'em, and that's how I got to go to some concerts (and with a fast redial finger!) ;D