I think I know the guy who does tailwheel endorsements out of C77. He is a really nice guy and is willing to help a lot of people out.
Depending on where you may be living there is a a flying club out of PWK which may get a little expensive from time to time due to fuel costs being so high in Chicago.
http://www.windycityflyers.com/ They do have quite the variety of planes but also depends on how much you would plan on flying. I looked into them but didn't plan on flying that often so it wasn't for me.
I normally rent out of KARR which is the SW suburbs of Chicago. 172P for $123/hr wet. Again this just worked for me because I wasn't planning on flying that much so a club was just not cost effective. If you have any questions feel free to ask. I grew up at KDPA and know the area fairly well.