Yes, I did file V7 over the lake.

It might depend on destination. Since Gary is close, they can get me
out of the system quickest by keeping me on the east side. If you were
headed for, say, Cincinnati, it wouldn't surprise me that they sent you
via Rockford. In fact, on a recent flight from Gary to Des Moines,
which is basically straight west, they sent me nearly to Rockford,
which is about 50 miles off course.