A timeless Engagement Session in Downtown Chicago


Chicago’s iconic spots make for a classic downtown engagement session

I can’t say this about many people, but I’ve known Holly since the first grade.   We went to the same school together all the way through 12th grade, before heading to different states for college.   When she sent out a facebook message last year announcing she was moving to Chicago with her fiance Rob to work at Lurie’s Children Hospital as a nurse practitioner, I was thrilled.  Holly’s always stood out to me as someone incredibly down-to-earth, genuine, kind, and joyful.

This past year, I’ve gotten to know Rob as her perfect match.  He’s laid back with a great smile and a touch of quirkiness. It’s not uncommon to catch them from the corner of my eye making each other laugh at an inside joke or affectionately holding hands.  I’m so happy to see my long-time friend paired with such a great guy.

Iconic Chicago Backgrounds

Since Holly and Rob were new to Chicago, for their engagement photos, they wanted a few of the most iconic Chicago backgrounds. I’ve spent 10 years in this city, so these spots aren’t as new and sparkly to me as the first time I visited.  So taking these two on a tour de force around downtown felt like I was seeing it through their eyes for the first time again.

Channeling Old Hollywood on the steps of The Art Institue

I’m a sucker for the Met Ball in New York. If there’s one event in social pages that I can’t ignore, it’s this one. I love the combination of theatrics and high-end fashion that inspires attendees outfits. We channeled the timeless glamour of the event on the steps of the Art Institute of Chicago. Then riding the Hollywood vibes, we headed over to The Chicago Theater for a few pictures at dusk with the sign lit up behind them.

Can’t skip Chicago’s skyline

After two stops, most grooms are usually ready to call it a day, but not Rob. With a boyish grin, he back in the car and said where to next. To the stars! Sorry, talk of Hollywood’s making me a bit dramatic. “Well you have to see the skyline at night from The Observatory,” I replied.

Off we went, zipping down lakeshore and cutting east toward the lake, circling past Soldier Field.

When we pulled up along the magnificent concrete steps leading toward the water, the city sparkling in the background, I once again saw the view threw their eyes. I still give it to Manhattan for the best skyline, Chicago’s no shabby second. We wrapped our whirlwind engagement session through Chicago’s downtown with our last few pictures capturing the buildings creating soft, glowy reflections in the water behind them. It was the perfect place to end.