Some couples want Chicago landmarks. The Bean, the Riverwalk, the skyline at sunset. And those sessions are great. But Carly and Alex had something different in mind. They wanted their engagement photos to feel like their life, and their life is in Wicker Park.
They have lived in the neighborhood for a few years now. They walk the 606. They have their regular spots. They know which places are worth the wait and which ones are open late. Wicker Park has that quality where the longer you live there, the more it feels like a small town tucked inside a big city.
I have been shooting in Wicker Park since I first started in wedding photography. My kids go to school there, so I know the neighborhood well. But it is actually rare that I shoot engagement sessions there. Most couples gravitate toward the lakefront or downtown. This session was a good reminder of why Wicker Park deserves more of them.
Everything you are about to see happened within about a half mile of their front door.
Six Corners and the Blue Line
We started at Six Corners, where Milwaukee, Damen, and North Avenue all come together at once. It is the kind of intersection that only Chicago produces. The Robey Hotel rises above the corner in the old Flatiron building, all angles and a historic landmark. Across the street, a former bank building now houses a newly reopened Barnes and Noble, a bookstore in a space that still feels like it has some history in the walls.
We spent some time shooting underneath the Blue Line tracks, right at the Damen station. The elevated structure gives you these great repeating lines, and the light that filters through the girders has a quality you cannot replicate anywhere else. Add in the street signage, the crosswalks, and the general movement of a neighborhood going about its day, and the whole thing starts to feel less like an engagement session and more like street photography. Which was exactly the energy Carly and Alex were after.
Street Art and Small Cheval
These two were not nervous in front of the camera. They were just having fun with each other, and it showed. The way they make each other laugh, and the way they look at each other when they think no one is watching…those were some of my favorite frames of the whole session.
Then we stopped at Small Cheval. If you have not been, it is becoming a Chicago institution: a smaller outpost of Au Cheval that does burgers and milkshakes and stays open late. I brought my own family there a few days after this shoot. The fact that Carly and Alex live walking distance from it is either a blessing or a problem, depending on how you look at it.
One of the things that makes Wicker Park a great place to shoot is the street art. Murals turn up on the sides of buildings, on retaining walls, in alleys. They change over time, which means every session looks a little different from the last. We stopped at a few spots along the way, including a mural of a heart tree near Ava’s Italian Ice, one of those neighborhood staples that locals know and tourists walk right past.
The 606 Bloomingdale Trail at Sunset
After a quick outfit change at home, we headed to the 606 Bloomingdale Trail for the second part of the session.
The 606 does not show up on many tourist itineraries, but if you live on the north side of Chicago, you know it. A former elevated rail line converted into a walking and running trail, it connects Wicker Park to Humboldt Park, Bucktown, Logan Square, and beyond. On a late September evening with the sun starting to drop, it is one of the more beautiful stretches of the city.
In Wicker Park, the trail crosses over Milwaukee Avenue on a bridge that is almost sculptural in how it sits above the street. That is where we finished the outdoor portion of the session. The setting sun came in at a low angle and hit the scene in a way that felt cinematic and a little dramatic: warm, directional light, the city spread out below, two people who clearly belong together.
Wolf and Company
We closed the night at Wolf and Company, one of Carly and Alex’s favorite bars in the neighborhood. It was a fitting end to a session that was built entirely around the way they actually live in this city.
Carly and Alex, thank you for letting me into your neighborhood and your story. I hope these photos feel as much like home as Wicker Park does to you. I can’t wait til next year to photograph your wedding!
If you are planning a Chicago engagement session and want it to feel personal…rooted in the places that actually mean something to you, that is exactly what I love to do. Let’s talk.
