Some engagement sessions feel like a love letter to a place—and Kieran and Rachel’s Chicago session was exactly that. These two call Chicago home, so when they asked if I would travel up for the day to photograph their engagement photos in the city they love most, the answer was an easy YES.

We spent an October day running all over Chicago, making sure we captured its energy, architecture, and iconic spots that matter to them. And honestly? It was perfect—crisp fall weather, beautiful light, and the kind of fun, effortless connection that makes photographing a couple feel like spending the day with old friends.

Our route was ambitious—in the best way.
We started at the Chicago Theatre, with its classic marquee glowing above us, then wandered to the Board of Trade Building for those cinematic city views. From there, we made our way through Millennium Park, surrounded by skyline and fall color.

Next, we stopped at Milton Lee Olive Park for quiet, lakefront moments, and wrapped up the evening at North Avenue Beach, where the city stretched behind them in all its blue-and-gold sunset glory.

One thing I loved most about this day: Kieran and Rachel were completely all-in. Running between locations, embracing the wind off the lake, laughing constantly, and trusting the process—every minute was easy and joyful. Their chemistry shines in every image.

And the best part?
I get to celebrate with them again next fall when they get married in St. Louis. I travel back to St. Louis often for weddings, and being able to document their story both in their current home of Chicago and in my hometown area makes their wedding feel extra special.

Kieran and Rachel—thank you for the adventure. I’m already counting down to your wedding day. Enjoy a look at some of my favorite moments from our day exploring Chicago together!