When people see these photos, they usually notice the vintage Cadillac, the oversized hat, or the classic black-and-white outfits first. What they don’t see are the weeks of planning that made this engagement session in Chicago come together. From building mood boards and virtually scouting locations from Kansas City to finding every outfit and accessory, booking the vintage car, coordinating hair and makeup, and completely rearranging our timeline the night before because of the weather, every detail had a purpose. This wasn’t about hopping on a plane and hoping for the best. It was about creating an experience that felt effortless, stylish, and completely true to them.
The Planning Behind This Engagement Session in Chicago
One thing I love about destination sessions is that they start long before travel day. Before flights were even booked, we spent hours building mood boards, scouting locations virtually, and figuring out exactly how we wanted the day to feel. Every outfit, shoe, and accessory was chosen with the locations in mind so the entire gallery would feel cohesive from beginning to end. The vintage Cadillac was one of my favorite details because it wasn’t just transportation, it became part of the story. Once we had the locations, outfits, and car booked, I built a timeline around the best light and travel between each stop so the day felt relaxed instead of rushed.
Why Chicago Was the Perfect Backdrop
One of the reasons I love planning an engagement session in Chicago is how much variety you can fit into one day. We started downtown with the Cadillac before heading to the Art Institute, where the gardens, fountains, and architecture gave us a completely different feel without ever leaving the city. Inside the museum, the marble staircases and galleries brought in a classic editorial look, while Tiffany & Co. and Navy Pier added even more personality to the day. Every stop felt different, but together they told one cohesive story instead of looking like a collection of random locations.
When the Best Plans Need to Change
The night before the session, the forecast completely changed, which meant our original timeline had to change too. Thankfully, every vendor was incredibly accommodating, so we shifted everything around and managed to finish every outdoor location before the rain rolled in. Honestly, that’s why I spend so much time planning. Destination sessions almost always come with a few unexpected surprises, but having a solid plan makes it easy to pivot without losing the vision. My couples get to stay present and enjoy the experience while I handle everything happening behind the scenes.
Thinking About Your Own Engagement Session in Chicago? Would Love To Chat!
Ashley Ice Photography | Kansas City and Destination Wedding Photographer
If you’ve been dreaming about an engagement session that feels a little different, I’d love to help you plan it. Whether Chicago has always been your dream location or there’s another city that’s meaningful to you, I’ll help with everything from location scouting and timelines to outfit styling and all the little details that bring your vision to life. The goal is never just beautiful photos. It’s creating an experience that’s fun, intentional, and feels completely like you, because that’s what you’ll remember long after the session is over. Head to my contact page so we can chat about the ideas you have! If you want to learn more about me and what I do, click here. Can’t wait to hear from you!
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