Chicago’s wind hits particularly hard when you’re standing on the elevated platform of the Harold Washington Library-State/Van Buren station after sunset, but photographer Nolis Anderson doesn’t seem bothered by the cold air slapping against his camo jacket.

As two trains have come and gone, Anderson hasn’t budged, gazing over the outer railing of the station, Canon PowerShot G1 X Mark III in hand. Still as the gargoyles looming above, Nolis scans the street below—waiting for a perfect shot.

“Oh man, I hope he comes over here,” Anderson says, eyeing a pedestrian in brightly colored clothing. “It would be so cool if he was crossing the street, the black asphalt with the white paint, with his orange jacket.”

As if on cue, the man in the orange jacket turns the corner and enters the frame of Anderson’s shot.

Known for capturing candid moments and sweeping, shadowy cityscapes, the Chicago native credits his best pictures to a mixture of experience and luck. “In street photography, you kind of just have to visualize the photo before it actually happens,” Anderson said. “Luck comes in when you have that person that just kind of walks into the perfect setting.”

Known for capturing candid moments and sweeping, shadowy cityscapes, the Chicago native credits his best pictures to a mixture of experience and luck. “In street photography, you kind of just have to visualize the photo before it actually happens,” Anderson said. “Luck comes in when you have that person that just kind of walks into the perfect setting.”

Anderson didn’t always plan to be a photographer. He bought his first camera and started shooting recreationally ten years ago. “I picked up a Canon film camera from a pawn shop for like fifty bucks,” he said. For years, Anderson thought photography would just serve as a creative outlet during pharmacy school. But eventually it became clear to him, and to a rapidly-increasing social media following, that photography was much more than a hobby.

“In street photography, you kind of just have to visualize the photo before it actually happens.”

Anderson didn’t always plan to be a photographer. He bought his first camera and started shooting recreationally ten years ago. “I picked up a Canon film camera from a pawn shop for like fifty bucks,” he said. For years, Anderson thought photography would just serve as a creative outlet during pharmacy school. But eventually it became clear to him, and to a rapidly-increasing social media following, that photography was much more than a hobby.

In the last five years, Anderson has shot some now-iconic Chicago photographs for major magazines and brands—from portraits of professional basketball players, to what became a viral image of Barack Obama during his farewell address. “That’s probably my favorite picture that I’ve ever taken,” he said, noting that the former president once lived ten minutes from where Anderson grew up on the Southside.

Having crossed many dream assignments off his bucket list, a lot of the work Anderson’s known for is similar to what he’s doing tonight: wandering into scenes and capturing beautiful, unguarded, in-between moments.

Armed with his PowerShot G1 X Mark III and ready to use the camera’s low light capability, the self-proclaimed night owl sets out during the golden hour so he’s ready to capture the city’s images at his favorite time: twilight. “It brings a really cool aura to the city that you just can't get at another time of the day,” he said. “You get that combination of the downtown city lights starting to turn on but you still have just enough light where it balances out just enough, where everything looks really clean.”

Walking north on Dearborn Street, Anderson pauses at the towering figure of “The Flamingo,” a 53-foot-tall, 50-ton, vermillion statue named for its abstract resemblance to the lanky bird.

While tourists are quick to hand off smart phones and run underneath the statue to have their pictures taken, Anderson knows the most interesting shot is from a distance, with the refection of the illuminated Willis Tower visible in the building behind it, and the image of the red bird caught in the puddle in front. “It’s kind of cool how a lot of photographers will see different angles,” he says, admiring the nuanced image on the camera’s Vari-angle LCD touch screen.

The camera's swivel screen feature comes in handy throughout the night. Anderson captures the dizzying blur of oncoming buses and subways from low angles he’d otherwise have to lie down to get—an unappealing task considering that “subway floors are really dirty.”

“You get that combination of the downtown city lights starting to turn on but you still have just enough light where it balances out just enough, where everything looks really clean.”

The camera's swivel screen feature comes in handy throughout the night. Anderson captures the dizzying blur of oncoming buses and subways from low angles he’d otherwise have to lie down to get—an unappealing task considering that “subway floors are really dirty.”

The Canon PowerShot G1 X Mark III’s ability to slow shutter speeds also helps capture the effect of the vehicles’ motion.

The next stop on Anderson’s journey is Millennium Park. Rather than joining the crowds at the Bean—which he says is best shot at the beginning of sunrise when light is just starting to reflect off the polished steel shape—he goes to the illuminated Crown Fountain, which features two 50-foot glass towers projecting bright images of Chicago residents’ faces.

“You get that combination of the downtown city lights starting to turn on but you still have just enough light where it balances out just enough, where everything looks really clean.”

Waiting for the perfect moment, Anderson catches shadowy forms of passers-by as they walk through the glowing shards of light.

After exiting the park, he walks down Wacker Drive, which begins at Lake Michigan and runs along the river. Punctuated with rows of bridges, this is Anderson’s favorite place to shoot. And the Canon PowerShot G1 X Mark III plays an important role in helping him blend into the scene.

“Usually when you're out shooting street photography, and people see somebody walking around with a big camera, they automatically get kind of weird or unnatural about it,” he said. “So walking around with this camera, it's just so small and so compact that people don't really pay mind to you. So I've been able to get pretty close to people in different situations with this camera.”

Turning on to State Street, he stops in front of the ornate Chicago Theatre to photograph the garish neon lights of its marquee—a landmark that locals and tourists consider to be the city’s unofficial emblem.

Anderson sees Chicago as the perfect in-between of New York and Los Angeles. “It’s the best of both worlds,” he says, climbing into a cab to Chinatown. "If you want to, you can go downtown and get the fast pace, and get the trains, and get the buses, and things of that nature. But you can also kind of go another route. You can go to the lake; you can go to the beach and you can kind of relax; or you can go outside of downtown, because Chicago is so much bigger than downtown.”

Anderson sees Chicago as the perfect in-between of New York and Los Angeles. “It’s the best of both worlds,” he says, climbing into a cab to Chinatown. "If you want to, you can go downtown and get the fast pace, and get the trains, and get the buses, and things of that nature. But you can also kind of go another route. You can go to the lake; you can go to the beach and you can kind of relax; or you can go outside of downtown, because Chicago is so much bigger than downtown.”

Climbing out of the taxi on Wentworth Avenue, in the shadow of the Chinatown Gate, Anderson recalls another time that brought him to this street.

"The Chicago marathon runners raced here," Anderson says, snapping a picture of Lucky Cats waving to him from inside a shop’s window. His first three years shooting the marathon, it was just him and a driver speeding through the city to get photos. "It was ridiculous. We’d shoot, go run back to the car, edit photos in the truck after driving to the next spot, and send them off so we could get back out." Last year, Anderson oversaw a team of nine photographers to chronicle the race—a testament to how far he’s come.

With the right tools, innate talent, an extraordinary eye, and a little bit of luck, Anderson is able to show the essence of Chicago to the rest of the world with the click of a button.