Old Town Chicago Engagement Photos
Hailey and Justin wanted something a little different for their engagement session. They were drawn to a casual Chicago neighborhood feel, and wanted to include a few of Chicago’s famous brownstone buildings. They whole thing to have more of a relaxed, lifestyle vibe than a traditional skyline-only shoot. We also knew we wanted to end up at the South Pond area of Lincoln Park, so I suggested we start out in Old Town, right next door.
That combo turned out to be perfect for an Old Town Chicago engagement session.
Brownstones, Cobblestones, and Dappled Light
Old Town has this quiet, lived-in character that you don’t really find in busier parts of the city. We wandered around and found a few beautiful historic brownstones to shoot in front of, plus some cobblestone alleys that gave the photos a real sense of place. It honestly just feels like a normal afternoon in Chicago, which is exactly the energy Hailey and Justin were going for.
The light cooperated too. We had a little dappled sunlight creeping through the trees as we worked our way through the neighborhood, which is one of my favorite kinds of light for an Old Town Chicago engagement. It’s soft, it moves, and it gives every frame a bit of texture without being harsh.
Hailey and Justin started in a casual street outfit.. jeans and gym shoes, the kind of thing they’d actually wear walking around their own neighborhood. That set the tone perfectly. It didn’t feel staged, it felt casual and relaxed.
A Relaxed, Fun Session
What really made this session work was how comfortable Hailey and Justin were with each other in front of the camera. They embraced it. They laughed, they leaned into each other, they didn’t overthink anything. I love all the expressions and smiles throughout these photos because none of it was forced… it’s just how they are together.
That ease is honestly the secret sauce of a good engagement session, whether you’re shooting in a neighborhood, on a rooftop, or anywhere else. When the couple is having fun, everything else falls into place.
A Quick Outfit Change and Off to South Pond
After we wrapped up their Old Town Chicago engagement, they changed into a second, slightly dressier outfit and we headed over to the South Pond area of Lincoln Park to finish things out.
On the bridge over the South Pond, we made sure to incorporate the John Hancock and the Chicago skyline into the background. Even though the whole point of starting in Old Town was to step away from the typical skyline shots, no Chicago engagement session feels complete without at least a few.
The boardwalk made for a timeless setting too — clean lines, soft greenery, all the focus on the two of them.
Sometimes we got a perfect gust of wind to blow Hailey’s hair at just the right moment, the kind of thing you can never plan for but always hope for. Those are the frames you look at later and think, yes, that one.
Why Old Town Works for a Chicago Engagement Session
If you’re planning an engagement session and you’re not sure you want a traditional skyline or lakefront shoot, an Old Town Chicago engagement is such a great option. You get historic brownstones, cobblestone alleys, tree-lined streets, and a neighborhood texture that feels distinctly Chicago without feeling touristy. And because Old Town sits right next to Lincoln Park, you can easily pair it with South Pond, North Avenue Beach, or the Lincoln Park Conservatory if you want a variety of looks in one session.
Hailey and Justin, can’t wait for your wedding next year! Thanks for trusting me with this one.
Looking for a Chicago wedding photographer for your own engagement session or wedding day? I’d love to hear about your plans.
