Long Read

Chicago Blues & Bitter Winds: A Freelance Photographer's Lament

@Clara Moon3/1/2026blog
Chicago Blues & Bitter Winds: A Freelance Photographer's Lament

okay, so. chicago. right? i’d heard the hype. deep dish, blues music, architecture that punches you in the face. what i didn’t hear enough about was the wind. seriously. it’s like the city’s perpetually exhaling a frosty sigh. i just checked and it’s…a teeth-chattering, nose-running kind of cold there right now, hope you like that kind of thing.


I’m a freelance photographer, you see. I chase light. I hunt for moments. And chicago…well, it’s got moments. moody, gritty, beautiful moments. but the light? it’s a challenge. everything looks like it’s perpetually filtered through a layer of grey. I spent a good chunk of my first day huddled in a doorway, trying to capture the reflections in a puddle without freezing my fingers off.

brown roots


I was supposed to be shooting a series on chicago’s street art scene - vibrant murals, hidden graffiti, that kind of thing. but the wind kept blowing my hair into my lens, and the light kept shifting. i ended up with a lot of blurry photos of brick walls and a growing sense of existential dread.

“Don’t bother with Wicker Park after dark,” someone slurred at me in a bar. “Too many shadows, not enough light. And the pigeons get aggressive.”


Seriously, the pigeons were aggressive. I swear one of them tried to steal my granola bar.

I did find some good stuff though. I stumbled upon a tiny blues club in Lincoln Park - Kingston Mines. The music was incredible, raw and soulful. The kind of music that makes you forget about the wind and the cold and the blurry photos. I managed to snag a few shots of the band, mostly silhouettes against the stage lights. They’re not perfect, but they’ve got something. You can check out some other blues venues here: https://www.timeout.com/chicago/music/best-blues-clubs-in-chicago.

brown and white house on brown grass field under white clouds and blue sky during daytime


I’m staying in a tiny Airbnb in Pilsen. It’s…charming, i guess? The walls are paper-thin, and i can hear my neighbor practicing the tuba at all hours. if you get bored, Joliet and Aurora are just a short drive away. I’m trying to find some decent coffee shops around here. I heard that Intelligentsia is the place to be, but the line is always insane. Yelp says it’s worth it, though: https://www.yelp.com/biz/intelligentsia-coffee-pilsen-chicago.

“Watch out for the El tracks,” a woman warned me, clutching her groceries. “They shake the whole neighborhood when they pass.”


She wasn’t kidding. My coffee nearly ended up on the ceiling this morning.

I’m starting to think chicago is less about grand gestures and more about finding beauty in the small, gritty details. A chipped brick wall, a puddle reflecting the city lights, a blues musician pouring his heart out on stage. It’s a city that demands patience, resilience, and a really good hat.

brown wooden ladder on brown brick wall


I’m heading to Millennium Park tomorrow, hoping for a break in the clouds. Maybe i’ll finally get a decent shot of “the bean.” Or maybe i’ll just end up shivering in a doorway again. Either way, it’ll be a story. You can find more info about the park here: https://www.cityofchicago.org/city/en/depts/dca/supp_info/millennium_park.html.

Someone told me that the deep dish pizza is overrated. I’m going to test that theory tomorrow. For science.


You might also be interested in:

About the author: Clara Moon

Making the complicated simple, and the simple profound.

Loading discussion...