Chicago area from the southwest - advice?

"bdl" writes:
Yeah I heard you. It was more of the "heck, why do they have me on a
270 vector STILL?" I wanna go south! I'm /G pick a point on the map,
I'll go there. It's nice and flat around here, I'm high enough to not
be an issue with any towers, but low enough that I shouldn't be in
anybody's approach path.

If you pass by some high rocks and start seeing an
endless stretch of water ahead of you, you have
probably been sent a bit too far west.

Even requested a more southerly vector from Chicago Center (I had been
on a 270 vector for that long) and it was at least another 15 minutes
before I could be turned south.

On an airline flight departing LAX, we were vectored west
over the ocean. After quite some time, the pilot told
the passengers that ATC had promised we could turn
east some time before getting to Hawaii.

Not complaining, was just curious as to the "box" ATC was working in.

I think the next time, I'll be departing VFR (weather permitting) with
a filed IFR clearance originating further down the road. When doing
cross countries I like to be in the system. It lets my family track me
on flightaware.com, I know I'll get flight following, and as you said,
I can always cancel.