If you’re on the hunt for Chicago engagement photos that feel full of personality, movement, and love, let me take you through Hannah and Jack’s unforgettable session. From Wicker Park engagement photos that featured their pup Louie to a wild, joy-filled dip in Lake Michigan at North Ave Beach, their session captured everything I love most about being a Chicago engagement photographer.

It may have been chilly for a May afternoon, but the warmth of their connection and their willingness to jump into freezing water made this session magic.

Exploring Wicker Park: One of the Best Chicago Engagement Photo Locations

We started our time together wandering through Wicker Park, one of my favorite neighborhoods for engagement photos in Chicago. The mix of historic charm, modern edges, and tree-lined streets gives it such a versatile look, there’s beauty everywhere. Hannah and Jack brought Louie along (their pup and unofficial co-star), and we let him lead the way as we explored some quiet pockets of the neighborhood.

The streets of Wicker Park offer the perfect blend of city energy and cozy corners, exactly what you want when planning Chicago engagement photos that feel unique and personal. And as a Chicago engagement photographer, I always recommend this area to couples who want a casual, stylish backdrop that still feels like a love story.

North Ave Beach Engagement Photos

After exploring Wicker Park, we headed over to North Ave Beach, one of the most iconic and best Chicago engagement photo locations for a view of the skyline and that crystal-clear lake. The water was extra blue that day, the sky glowing with late-afternoon sun.

But the moment that made the session unforgettable? Hannah and Jack jumped in. Fully clothed, fully committed, and fully freezing and yet it felt like the most honest testament to their love: bold, fun, and deeply in tune with each other. As far as engagement photos in Chicago go, this one will be hard to top.

Hannah and Jack’s Story

Hannah and Jack met on Hinge in 2022, shortly after Hannah moved back to Chicago. She had spent the last 10 years in St. Louis coincidentally where Jack was born. Their shared Midwest roots made for an easy connection, and they quickly found their rhythm. Jack had grown up in Grand Rapids, and they’re now planning their wedding there, ready to create new memories in a city full of family history. Their first date was at a wine bar in Lincoln Park. Jack, sweet and a little nervous, showed up early. Hannah, running on classic Hannah-time, showed up ten minutes late.

In October 2024, Jack proposed on Mackinac Island during a quiet hike, just the two of them… and Louie! With their pup in a backpack peering over Hannah’s shoulder, Jack popped the question at a peaceful overlook. They spent the next hour soaking it all in before heading back to their hotel to call their closest people. They kept the news between just the two of them for a whole day, a detail Hannah says made the moment feel extra present and special.

Now, they’re building a life in a new neighborhood with Louie as their sidekick and Grand Rapids in their hearts for the next chapter.

Thinking About Engagement Photos in Chicago?

If you’re looking for the best Chicago engagement photo locations, pairing a cozy neighborhood like Wicker Park with a wide-open space like North Ave Beach gives you so much variety. I always encourage couples to think of their session as a mini adventure especially if we can include your dog, a dip in the water, or just your favorite neighborhood coffee shop.

Whether you’re into historic buildings, quiet streets, or wide lake views, there’s no shortage of incredible spots for engagement photos in Chicago. And if you’re someone who wants photos that feel true to you, full of connection and candid moments, you’ve found the right Chicago engagement photographer. Get in touch here!

I cannot wait to celebrate these two at Venue3Two next summer with Amusé Event Co!