Liset and Andrew’s Chicago engagement session was one of those magical evenings that proves sometimes the best plan is no plan at all. What started with locked gates and unexpected events turned into an unforgettable adventure through downtown with these two, ending in golden light on the sand at Montrose Beach. As a Chicago wedding photographer, these are the moments I live for, when the unexpected turns into something even more personal.

How They Met: From Valpo to Tequila Dates

Before their engagement photos in Chicago, Liset and Andrew’s story began at Valparaiso University in Indiana. While they were in the same friend group for years, it wasn’t until after college that sparks really flew. Their first “date” was classic: tacos and margaritas. Although Liset didn’t realize it was a date at first (sorry, Andrew!), it turns out it was the beginning of forever. Now, one thing they’ll both admit? They’ve got a soft spot for tequila shots, whether celebratory or just for fun.

A Downtown Chicago Proposal

Chicago has always held a special place in their hearts. So when Andrew planned a staycation, Liset had no idea a proposal was coming. On a walk from the Chicago River to the planetarium, Andrew popped the question in front of the skyline they both love so much. A friend captured the moment, but the night was intentionally left just for them; romantic, intimate, and oh-so-them.

Finding the Best Places for Engagement Photos in Chicago (Even When the Plan Shifts)

We originally planned for their engagement pictures at the Chicago Botanical Gardens and then at the Art Institute of Chicago, specifically the iconic South Garden. Unfortunately, it was unexpectedly closed, so we made a quick pivot to Lurie Garden in Millennium Park. But just as we started, an event had us moving again. As any seasoned Chicago engagement photographer knows, flexibility is key and honestly, I love the challenge.

We wandered nearby, found stunning secret corners tucked into the city, and leaned into spontaneity. These are the moments that set couples apart. Liset and Andrew trusted the process, stayed connected to each other, and the images reflect that energy. Their chemistry and laughter turned what could have been stressful into something effortlessly beautiful.

Montrose Beach Engagement Photos to End the Evening

We wrapped up the evening with Montrose Beach engagement photos; a perfect, casual way to end their session. The golden glow of the sun, a soft lake breeze, and the relaxed pace gave space for barefoot walks and stolen kisses. As a Chicago wedding photographer, these are my favorite kinds of moments: the in-between, the real, the joy that shows up when you’re just being yourselves.

Planning Your Chicago Engagement Session

Whether you’re dreaming of art institute of Chicago engagement pictures, lakeshore strolls, or discovering hidden gems downtown, working with Chicago engagement photographers who know how to adapt and lead calmly makes all the difference. If you’re looking for someone who can roll with the unexpected and still give you jaw-dropping photos, you’re in the right place.

Liset and Andrew’s session is the perfect reminder that the best places for engagement photos in Chicago are the ones where you’re fully present with each other, planned or not. I cannot wait for their Chicago wedding next spring!

Get in touch here!