Ok, I'm going to try and give a little more information about these various stations per marsgov's suggestion:
WUSN-FM, CHICAGO, is also known as US99.5. They have a website, but no way to request songs online unless you feel like emailing a DJ personally.
http://www.us99.com/ Best bet: the old-fashioned phone.
WXXQ-FM, ROCKFORD, aka Q98.5, has an e-quest button on their site
http://www.q985online.com/equests.shtml, so email away!
WUSY-FM, CHATTANOOGA, aka US101. You can listen live on their website
http://www.us101country.com/pages/contactus.html, but still have to phone in requests.
WNCY-FM, GREEN BAY, aka Y100 100.3. Same deal, listen online but phone in requests or email DJs directly.
http://www.wncy.com/ WMAD-FM, MADISON, aka 96.3 Star Country. See previous comment...
http://www.wmad.com/main.html WWQM-FM, MADISON, aka Q106.3. Listen live and email requests from the home page:
http://www.q106.com/ KEEY-FM, MINNEAPOLIS, aka K102. Listen live and email requests to:
http://www.k102.com/pages/info.html?feed=206724&article=2453980 KWJJ-FM, PORTLAND, aka 99.5 The Wolf. Back to emailing DJs or calling in a request.
http://www.thewolfonline.com/ Whoo! So far Rockford and Madison Q106.3 are the winners for easiest to navigate sites...