Chicago

This industrial powerhouse has lots of cool history, and tons to do. The jazz and food scenes are world-renowned, so fans of either should check this one out in summer when walking down by Lake Michigan is an awesome way to begin or end a day.

I’d recommend staying at one of the many hotels and rentals within walking distance of Navy Pier: it’s a relatively affordable city and being able to walk instead of driving will help you get a much better sense of the sheer vertical scale of the place.