Moonstruck - 80's New York. Not only my favorite movie, but such a rich detail of 80's New York...
Adventures in Babysitting - 80's Chicago. This one is a real adventure around the Chicago cityscape. Chicago was presented as modern, affluent AND gritty. Those skyscraper top scenes are worth watching alone.
Ferris Bueller's Day Off - 80's Chicago. Very similar to Adventures in Babysitting, but with more focus on high school kid shenanigans. I used to live for the parade scene in downtown Chicago...