Chicago in the winter isn’t for the faint-hearted. The streets are cold, the light fades fast, and if you’re standing still, you’re doing it wrong. But that kind of weather has its own appeal stripped down, honest, and just unpredictable enough to make things interesting.

We met near the Art Institute ,cClassic architecture, soft afternoon light, and we need to keep moving from the cold. No overthinking. Just walking, pausing when the moment called for it, and letting them settle into each other naturally. We wrapped with hot chocolate near Millennium Park. Call it practical romance.

This wasn’t our first time working together. I photographed the bride-to-be’s brother’s wedding a few years back one of those early jobs that stayed with me for all the right reasons. Getting the email from her felt like a full-circle moment. There’s something about returning to familiar families that adds depth it’s not just about documenting a new story, but continuing one. I’m looking forward to seeing everyone again on the wedding day.

When I shoot engagement sessions in Chicago, I keep it efficient and effortless. No elaborate set-ups, no awkward posing marathons. I’ll give you just enough direction to make it easy, then step back and let you take it from there. The goal is always the same: images that look and feel like you.

If you're planning a winter engagement session, a downtown elopement, or a city wedding, don’t let the season scare you off. The best photographs aren’t always taken on perfect days they’re made when people show up, trust the process, and let the story unfold.