The provider is not important, it is the cable/satellite box they provide that is important. And incompatible is the wrong word, the Slingbox is compatible with all set-top-boxes. What you probably mean is 'not supported', in that the remote for the set top box is not in the database. If that is the case I can probably produce you a Custom Remote.
I setup my RCN cable box using component cabling using a slingbox 500 but I cannot watch tv on my iPhone or iPad.
Please let me know which Chicago cable provider is compatible with slingbox 500! I think only Directv works!
Let me know if other providers from Chicago works for you