Rachel and Brandon’s Engagement Photos in Chicago

FILED IN: Engagements

May 10, 2025

In May, I met up with Rachel and Brandon to capture their engagement in the city they love! I wanted to naturally document the time together with very little prompting in order to create timeless and authentic photos. We did just that and it was a beautiful engagement session in Chicago!

One thing that really stood out to me during their session was how natural their love felt. After being together for nearly a decade, of course you’d feel comfortable with each other. But Rachel and Brandon’s interactions felt so sweet, natural, and authentic. I love love LOVE seeing that. And I LOVE getting to document it!

Their Engagement Photos in the City of Chicago

Our first location was a street they often take walks on near their apartment. It truly was such a cute spot to start their session. We then passed by Wrigley Field, home of the Chicago Cubs and took some photos there. Rachel and Brandon spend a lot of time there taking in baseball games, so we wanted to document that! We even got their lab for a few photos because it’s always a MUST to get a little family photo with your dog! 

The main goal of the second location was to capture this couple in Chicago alongside the water during blue hour. WE ALL KNOW HOW I FEEL ABOUT BLUE HOUR — I LOVE IT!

We popped a bottle of champagne and headed to our final location of the night, a bar nearby that they enjoy going to. The vibes were so good! I always love the outcome of taking photos at restaurants or bars that a couple frequently visits.

Their Longstanding Love Story

Rachel and Brandon are such a sweet couple. They grew up in the same town in Michigan and met in middle school. But, they didn’t start dating until their freshman year of college at Western Michigan University. They’ve now been together for nine years! They really enjoy spending time together, finding new restaurants, and of course going to Cubs games.

About three years ago they moved to Chicago together — and they absolutely love it there! It was a blast taking engagement photos in Chicago of their love story in the city they’ve also fallen in love with.

Last December, Brandon proposed to Rachel in their home, complete with a light-up “marry me” sign. These two will be getting married at the end of this year in Saugatuck. I’m so so so excited to be a part of their wedding day! 

Looking for an engagement photographer in Chicago, Michigan, or beyond? Let’s chat!