Ok, here's the answer:
The five cities in which I spent the night:
Chicago
Cleveland
Indianapolis
Miami
Boston (I live in Charlestown, which is in the city of Boston -- but no whining: the winner didn't have Boston on his list)
The winner:
ROBERT LG
who got three right: Miami, Chicago, and Cleveland.
I'll be sending off a package of goodies to Robert shortly.
Thanks for playing!