Engagement at the Wrigley Building & North Avenue Beach

Kaylee and Jake’s summer engagement session was the perfect love letter to Chicago! Kaylee is a Chicago girl through and through, while Jake is from St. Louis. In a fun twist of fate, she attended the University of Missouri, and he went to the University of Illinois. Somewhere after that, they met, fell in love, and are now planning their wedding day!

Although they currently live in St. Louis, it was important to Kaylee that their engagement photos reflected her ‘sweet home Chicago’. Choosing two iconic locations made the session feel meaningful, personal, and very them. I loved helping them choose these locations!

Wrigley Building & North Avenue Beach Engagement Photos 

We began the evening at the Wrigley Building, one of my favorite downtown locations for engagement sessions. In the early evening during summer, the sun sits just above the tops of the buildings, creating such a beautiful glow! It really is the perfect balance for romantic portraits in the heart of the city.

From there, we hopped in a rideshare and headed to North Avenue Beach. (Pro Tip: Castaways is always a great landmark to use for GPS!) It truly was THE MOST PERFECT SUMMER EVENING! Once we arrived at North Avenue Beach, our walk toward the lake was full of energy with beach volleyball, bikes, and summer activity all around. As we reached the wall that separates the beach from Lake Michigan, the skyline opened up in front of us just as the sun began to set.

And can we talk about Lake Michigan for a moment?! It photographs the most beautiful shade of blue. No special edits required! That soft baby blue color is completely natural and just one of the things that makes Lake Michigan so unique compared to other Midwest lakes. On this particular evening, the views could not have been better!

Kaylee and Jake were relaxed, joyful, and so easy to photograph at their Chicago engagement session. The combination of classic architecture, skyline views, and summer light made this session feel timeless and fun all at once.

I am already counting down to their wedding in September 2026 at Makray Memorial Golf Club. If their engagement session is any indication, their wedding day is going to be amazing!

Kim Ritchie Photography is a wedding and portrait photographer based in Chicagoland, specializing in weddings, seniors, and corporate headshots captured in a timeless style. Want to work together? Reach out here and follow along on social to see what’s happening behind the scenes!

Engagement Photos at the Wrigley Building & North Avenue Beach | Chicago Engagement Photos | Chicago Wedding Photographer | Chicago Engagement Photographer