We Asked Nine Photographers for the Ultimate Chicago Street Shot

From street corners to secret hideaways, here’s your checklist

By Moira Lawler

We Asked 9 Photographers for the Ultimate Chicago Street Shot
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15 March 2017

Raine or shine or zero degrees and snowbound, Chicago is a beautiful city to look at.

Look no further than your Instagram feed for proof: The expansive skyline view from the Adler Planetarium; the lakefront on a sunny day; Lincoln Park with the Hancock towering in the distance.

But for a truly exceptional shot, you need to look beyond the obvious.

So we asked nine photographers for their opinion on the ultimate Chicago shot.

From secret alleyways to unassuming street corners, here’s where they go to capture the city in its most mesmeric light.


That Parking Garage in the Loop.
“My favorite spot for amazing photos is from inside the parking garage at the northwest corner of Clark and Lake. I think it’s worth mentioning that the legality of this is a bit of a grey area. It’s not for the faint of heart, but it’s definitely worth it. Take the elevator to one of the top floors. You’ll notice that the garage is open to the air, with mirrored glass covering most but not all of the window openings. If you walk to the south-facing side of the building, you can (very carefully) reach your camera out and get a beautiful shot in both directions down Lake Street, with the L tracks below and a nice mirror reflection off the glass.”

— Alex Sheyn, @theonlygoodalex

A post shared by Steve (@hip_hipster_ray) on


Where the 606 Intersects Milwaukee Avenue.
“I prefer to take a walk or bike ride along the trail around sunset and watch the activity looking south down Milwaukee Avenue toward downtown. The light is nice that time of day, and there's a lot of activity since many people are returning from work. The L also passes nearby and looks cool against the backdrop of the city's skyline.”

— Steve Kuzminski, @hip_hipster_ray


Looking South on LaSalle Street in the Loop.
“The Board of Trade Building is at the end of the road, and it provides this feeling of old-school beauty. With the Ceres statue hanging from above, I feel like I’m in Gotham and Batman might swoop in at any moment.”

— Matt Weitz, @mattbweitz

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State and Lake L Station.
“It's next to the Chicago Theatre, so you can have some fun figuring some ways to incorporate that into your shot. I've had the best luck during the blue hour (the hour after sunset) on a clear or partly cloudy day so you get that pop of blue from the sky. For a good chunk of the year, this happens to align with all the 9-to-5ers getting off work. More people equals more subjects!”

— Andrew Glatt, @andrew_glatt


West Chicago Avenue Over the Kennedy Expressway.
“On the south side of the street, you'll find a hole in the fence that lines up perfectly with the center of the highway and the Chicago skyline right behind it. Shooting here is a winner any time of the day, but I recommend going during sunrise or sunset to add a more interesting element.”

— Michael Salisbury, @msalisbu

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Pickwick Coffee Roasting Co.’s Alley.
"There’s a beautiful side alley right off Jackson Street [between State and Wabash] that you might just miss if you don’t take a look around. Down the alley holds a small hole-in-the-wall coffee shop with string lights up above that fill the alley with a warm orange glow.”

— Johnny Fan, @johnnyfan

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One of the LaSalle Intersections Near the Chicago Board of Trade
“Not to sound cheesy, but you really do see all walks of life over there. You've got dressed-up white-collar workers, families, tourists ... the list goes on. I love shooting that spot during the summer when the morning sun is hitting the street with harsh shadows.”

— Graham Chapman, @gh_chapman


Sangamon Between Hubbard and Kinzie
. “The Fulton Market area of the city is very unique and removed enough from the city center that you can capture a perfect shot with the Chicago skyline in the background.”

— Julia and Jake, @chicagoculturecouple


Wherever the Light is Right.
For me, there isn't a particular place to shoot the best street photo because I honestly believe that Chicago has character everywhere you go. I also think that the most important characteristics, aesthetically, for a dope street photo are light and shadows. I think if you find this, regardless of where in Chicago you may be, then you can produce a legit shot.”

— Danny Mota, @dannymota

Main photo: Adam Alexander Photography

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