Fall has always been a popular time of year for engagement photos, and it’s still in full swing! One of my first sessions this season was with Jessie and Rick in Humboldt Park. Many of you know I call this neighborhood home, but it also happens to be where Jessie lived when she and Rick first got together! I was thrilled to take a trip down memory lane and visit some of their favorite local spots.

Chicago Cocktail Bar Engagement

I met these two at one of our mutual favorite spots, The California Clipper on a lovely October evening. If you’re in Chicago and have never been to the Clipper, I highly recommend checking this place out! Not only is this bar almost 100 years old, they also have live music most nights and a cocktail list worth sampling. But – I digress!

Jessie and Rick were as adorable as ever, and I was just a little bit obsessed with Jessie’s engagement ring (Rick designed it himself!). After a couple of mocktails and some stellar dance moves, it was time for a quick outfit change and stroll down California Avenue.

Humboldt Park Engagement Photos

One of my favorite things about this neighborhood is that it never gets boring. There’s a mix of buildings and businesses that have been in Humboldt Park for decades, but also new places popping up all the time. California Avenue is particularly photogenic – especially for street art! Of course we had to stop for photos with murals by local artists Sick Fisher and Jason Brammer. Finally, we arrived at Humboldt Park just in time for golden hour! Jessie and Rick were a breeze in front of the camera, and I could not be more excited for their wedding day next year 🙂

Jessie and Rick: Your Humboldt Park engagement session was a dream! Can’t wait to do it again next year!!