In or around Chicago will travel longer distances for longer encounters. For example, as I am based in Chicago proper, I will travel to the suburbs for a 4 hour dinner/long lunch date minimum, and to Rockford or as far north as Milwaukee or Madison for a clock free or overnight minimum.
This obviously depends on the lady, but if there is one who piques your interest, go ahead and shoot her an inquiry to see what kind of encouragement she might need to take a little road trip.
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