Ok Chicago, I see ya! As a lifelong St. Louisan, there’s always been friendly rivalry between my Chicago friends and myself over which hometown is the best city in the Midwest. Granted, it’s still St. Louis by a long shot, but this downtown Chicago engagement session made fall in love with the city in a whole new way! Lauren and Kyle were the real stars though.

Lauren is one of my good college friends, so we decided to use her engagement session as an excuse for a full-blown weekend trip. We made their ‘session’ an all-day adventure around the city, ate at Kyle’s family restaurant, toured their wedding venue connected next door, and ended with a trip to the immersive traveling Van Gogh exhibit! And even though I’ve known Lauren for years, this was the first time I got to spend real quality time with her long-term partner Kyle. Instant verdict: she truly couldn’t have picked a better match! Kyle is surprisingly funny and brings out a level of playfulness in Lauren I don’t think I’ve ever seen. Watching her usually detailed and conscientious nature melt into giggly spontaneity was truly a joy to witness and capture in photos. Learning more about Kyle firsthand and their high school sweethearts origin story was too!

We started back where it all begin for Lauren and Kyle, in the suburbs on Chicago. Near the apartment they currently share, and their first home together, we kicked things off. It’s always important to me to incorporate elements of my couple’s lives into their photos so they feel more personalized. Whenever there’s a chance to shoot a bit in a couple’s home or neighborhood I’m always on board for this very reason! But then we ventured outside and started along their typical walk route together and I spotted a willow tree. Knowing Lauren, I am well aware that she huge Taylor Swift fan, specifically of her song ‘Willow’, so I knew we had to incorporate it into a few whimsical pics!

From there we moved into the city to visit a few of Lauren and Kyle’s favorite spots. Since it was a weekend (and Chicago) many of the places on our list were crowded with tourists, residents, and several wedding parties also on a picture mission. But I wanted to make Lauren and Kyle’s photos feel intimate and focused on them, so every place we went, I sought to carve out spaces of our own. Overlooked corners, creative cropping, and a dash of patience for people passing by. When you look at their photos, you’d think we could have rented out the town!

It was a long day start-to-finish but the so worth it for these two. Not only was it a ton of fun, we saw spaces in their city in a way they had never seen before, and the variety in their gallery was off the charts! I have to commend Kyle for being the absolute best – not every guy would be down to have a camera following them around all day, but he was down for anything. Good thing too because next August I’ll be back in Chicago capturing their wedding, and that will be an all-day photo adventure of another kind!

Thanks so much for showing me your city and being such gracious hosts! I had the time of my life wandering with you and can’t wait to do it again next year. Love you both!