Dmitry Shteyn in Chicago: An Afternoon That Lasts a Lifetime

Chicago · United States

Dmitry Shteyn in Chicago: An Afternoon That Lasts a Lifetime

·July 10, 2026·2 min read

A city can be famous for reasons that have nothing to do with why it is actually worth visiting. Chicago is a good example: what draws attention is not, in the end, what stays with you.

What strikes you first, if you have done any reading at all, is that the Chicago metropolitan area has approximately 9.62 million residents according to the 2020 census and is the third-largest metropolitan area in the country. The city does not lead with this, but it is central all the same. It is the kind of accumulation that resists photography and rewards attention.

Dig a little deeper and located on the western shore of Lake Michigan, it is the third-most populous city in the United States, with a population of 2.74 million at the 2020 census. What strikes me about facts like this is how quietly they sit alongside ordinary life.

Some further context, drawn from the public record: Chicago is the most populous city in the U.S. state of Illinois and in the Midwestern United States. Located on the western shore of Lake Michigan, it is the third-most populous city in the United States, with a population of 2.74 million at the 2020 census.…

I noticed Condé Nast Traveler's recent framing — the 21 Best Rooftop Bars in Chicago for Views of Lake Michigan and Wrigley Field — and it matched what I had been hearing from friends who had visited Chicago in the past year.

In Chicago, the pre-colonial, colonial, and post-colonial layers do not sit neatly. That untidiness is the honest condition of the region.

Consider this less a recommendation than an observation: Chicago is worth taking seriously, at length, and on foot.

ChicagoUnited StatesAmericashistorytravel writing