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There is an Expert Travel Planner, and several versions of Expert Maps,
Windows based programs, which are quite good for what they are, and not
very expensive, say $15 to $50 max. I do not believe they go into the
detail of city maps.
 
There is a CD ROM from Deloram, Freeport ME that
covers the USA and has very detailed city maps; it seems a great
program.  They also do a VERY good world atlas.  The cost of these are
something like $150 each but you better check with them.  If I had CD I
would certainly have both of those discs.
 
Good luck.