Callie + Jess | Engagement Session in Downtown Chicago

Callie and Jess’ engagement session in the beauty that is downtown Chicago was a DREAM come true! These two are such stunning and incredible people, and the adoration they share for each other is seriously on another level. The two first met freshman year of college, but it wasn’t until years later that they finally left the friendzone and began dating. Fast forward a bit, and with their wedding now on the horizon for May of 2024 I was so excited to photograph their engagement session and get to know them. We got to explore some of my favorite spots in Chicago for their session and I cannot wait to show you all the highlights!!🀩

two signature drinks during and engagement session with the engagement ring on a Chicago bar

Fun in Chicago’s Merchandise Mart

Our adventure began at the gorgeous Merchandise Mart, specifically inside the ever so classy Marshall’s Landing. We purposely started our session with a drink at the bar to loosen up their nerves for the rest of their engagement photos. Luckily Callie, Jess and I all clicked SO fast and they were warmed up and ready to go in no time! After their drinks we made our way out of Merchandise Mart to continue their engagement session by exploring downtown Chicago. Of course before we began wandering we HAD to get some photos outside of Merchandise Mart though! The building’s architecture is stunning and was the perfect backdrop for these two beautiful people.

Three images side by side of a couple with a girl in a black dress and a guy in a suit sitting in a Chicago bar drinking their favorite drinks during their engagement session
fiancΓ©e leans up against her partner at a Chicago bar while sipping drinks
Engaged couple sits on gold and marble steps at Merchandise mart during their engagement session in downtown chicago
an engaged couple sits in an amphitheater in Merchandise Mart Chicago
an engaged couple stands holding hands outside of the Merchandise Mart building in Chicago during their engagement session in downtown Chicago
Couple walks towards the camera wearing black outfits holding hands and laughing at each other outside of the merchandise mart building in downtown Chicago
A fiancΓ© holds onto his fiancΓ©e making her laugh close to the camera during their engagement session in downtown Chicago
Couple holds one another standing outside the Merchandise Mart building in downtown Chicago
fiancΓ©e kisses his future wife on the cheek outside of the art deco building in Chicago
two photos of a couple laughing and kissing in front of a gold elevator in the Chicago board of trade building
A couple stands along the river walk in Chicago fro their engagement session
two images of a couple kissing and holding one another on the Riverwalk in Chicago for their engagement session.

Their Engagement Session in Downtown Chicago

Before we got into the next part of their session it was time for a quick wardrobe swap. I LOVE when my couples have multiple outfits for different portions of their session. It gives the album more variety and really lets the couple show off their style in their own ways. Both of Callie and Jess’ outfits complimented the other so well that it’s impossible for me to choose a favorite between the two! I also wanted to give a quick shout out to Jen Brown Makeup for the top notch work with Callie. 

With us exploring downtown Chicago for the remainder of their engagement session we were able to capture some truly awesome portraits in the city. From the Chicago River, the iconic skyline, and Wells Street Bridge, there is just SO much to see and love about the Windy City!!

A couple stands holding hands and kissing on the Dusable bridge in Chicago for their engagement session.
A couple in casual attire walks while holding hands during their Chicago engagement session on a bridge over the Chicago river.
Two images of a couple kissing and holding one another on a bridge over the Chicago river.
three images of a couple holding one another, kissing and holding hands while walking along the Chicago riverwalk.
A couple holds one another on a bridge over the Chicago river during their downtown Chicago engagement session
A couple holds one another while walking across the Lasalle street bridge during their engagement session at the Chicago riverwalk
Fiances kiss while walking over the Lasalle street bridge in Chicago during their engagement session

I am so happy that I was able to capture Callie and Jess’ engagement session in downtown Chicago, and even more excited for their wedding day come May of 2024!!😍 Their engagement session was incredible from start to finish so I can’t wait to photograph all the joy of their wedding day. For a look at more galleries and love stories like Callie and Jess’ check out my blog page. If you’re ready to book me as your photographer be sure to send me an inquiry through my contact page so we can reserve your date today!

A couple walks holding hands under the L in Chicago looking at one another during their downtown Chicago engagement session
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Cassidy + Andrew | Chicago Proposal