Such a tax might face a constitutional challenge. Governments cannot aim a tax specifically on newspapers, though newspapers are subject to general taxes. It's not clear to me how a bullet tax or something similar would fare since it is more indirect in nature. Still, does Chicago want more litigation on this matter?
Jim's Rules of Carry: 1. Any gun is better than no gun. 2. A gun that is reliable is better than a gun that is not. 3. A hole in the right place is better than a hole in the wrong place. 4. A bigger hole is a better hole.