Masks of Chicagoland: Portraits of Masks in The City

3 min readApr 27, 2020

Edit: Take a look at parts 2 and 3 of this series for more portraits.

One thing is clear. COVID-19 will change America. We’re too close to it to see it now, but everyone knows it’s coming. There’s a lot to talk about: politics, economics, culture, et cetera.

One thing we know now. Masks proliferate on streets where we once gave the side-eye to anyone silly enough to cover a face in public. Over the last three weeks, I have taken street portraits of people who happen to walk by me. Here’s what I’ve learned.

The City In Their Faces

Chicago isn’t just politics, policy, or economics. We can see our city and our communities in the faces of people who live and work there.

A close up photo of a woman in a blue medical mask with sunglasses that reflect the street and a homeless man. — Michigan Avenue reflected in her sunglasses.

A woman in a red coat, orange hat, and sunglasses wears a white cloth mask while we see the lake’s reflection. — A walk near the lake brings a time for reflection.

A woman wears a pink buff while out for a walk on a sunny, cool day. — A pink buff protects this Gold Coast walker.

It’s All In The Eyes

The face shows emotion, even when we don’t want it to. A flash of a smile. A frozen look. I used to think about the smile, the frown, or the pursed lips, but I can now see that our eyes are just as important. Even with half our faces covered, you can still see the smile beneath the mask.

A couple stands outside of Grant Park in Chicago.

A woman wears a Joker themed mask outside of Oz Park in Lincoln Park, Chicago. — Near the edge of Oz Park in the Lincoln Park neighborhood of Chicago.

A medical mask and sunglasses can’t cover up her expression.

A man with a black hat and a narrow green mask.

Chicagoans Will Talk To A Stranger

City denizens are well known for ignoring the world as they speed walk down busy, or not-so-busy, streets. The people of Chicago didn’t fit the stereotype. Nearly everyone stopped long enough for me to ask permission for their portraits, and most were happy to give me a few seconds for a photo.

A Chicago Transit Authority worker poses for a portrait while waiting for his bus route to start. — A Chicago Transit Authority workers poses while he waits for his bus route to start.

An elderly woman wears a mask improvised from a scarf. — On the north side of Michigan Avenue, a local goes for a walk on a sunny day.

A pair of young women stop to smile (maybe) for the camera, perhaps with a hint of ennui. — A pair of young women stop for a portrait in the Gold Coast neighborhood of Chicago.

Masks Are More Than Protection

While many people wore the standard blue medical mask, more and more walk, run, or bike with fashionable cloth masks in a variety of patterns and shapes.