Cloudy Engagement session at Milton Lee Olive Park | Stephanie and Nick

I was so excited to hang out with Stephanie and Nick again for their Chicago engagement session. After meeting up once to chat about their wedding day, it was such a treat to photograph them at Milton Lee Olive Park. This spot is a favorite of mine for both engagement sessions and wedding portraits, especially with that stunning skyline in the background. Even on a cloudy day, Chicago knows how to show off.

From Chicago to Wisconsin with Love

Stephanie and Nick have one of those classic meet-cute stories. They met randomly at a party, thanks to some mutual friends who had a good feeling about them. With a little help from the universe (and a lot of effort on their part), it all fell into place. Nick told me, “I took a leap of faith and flew to NYC to take her out. It was an amazing first date. We stayed up all night talking and dancing all weekend. Turns out, it would be our last 'first date' ever.”

Through quarantine, cross-country moves, and everything in between, Stephanie and Nick have built something solid. I was beyond excited to meet them in Chicago while they plan their Milwaukee wedding at the Wisconsin Club. That’s not just their future wedding location, it’s also where they celebrated their engagement. After proposing at North Avenue Beach (another favorite engagement spot), Nick surprised Stephanie with a trip to Wisconsin where all their friends and family were waiting to celebrate.

Dressed to Match the Skyline

For our session at Olive Park, Stephanie looked stunning in an emerald green dress while Nick rocked a navy blue suit jacket. Their outfits popped beautifully against the lake and city skyline. I love when couples choose looks that feel true to them—and these two were glowing the entire time. After the session, we grabbed drinks at a nearby bar and finalized their wedding day timeline. All of my wedding collections include timeline consultations, and it always helps make the day smoother when we’re aligned on expectations.

Next Stop: Milwaukee

I can’t wait to head back to the Midwest and photograph Stephanie and Nick’s summer wedding at the Wisconsin Club. If their engagement session was any indication, it’s going to be joyful, stylish, and full of heart.

Looking for a Chicago engagement session with skyline views? Milton Lee Olive Park is a stunner, and I’d love to help you plan your session there. Or check a few other engagement session blogs below!

xx,

Jennifer Lourie