*from Jun-Sep!

Is it cheating to nominate a city for only a few months of the year?

Probably, but we make the rules around here, so full speed ahead.

As someone hailing from outside the US, the image I had of Chicago was gritty people in big coats scurrying through snowy streets in desperate search of hot dogs and whiskey. A scene that gives a very distinct feeling of being appropriately rated.

Imagine my surprise rolling into town in blazing early July sunshine, finding myself surrounded by striking public artworks, watching a movie under the stars, and saying in shock "is that... a beach?!"

It was, indeed, a beach. And it was glorious.

Our tip: ...used to be "cocktails are cheaper than tourism, so hit the Signature Room for views instead of Willis Tower" - alas, Sig Room RIP. So: we've heard good things about the Riverwalk.

Underrated Cities