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I love covering a proposal. A proposal in Chicago? You bet I’d drop everything to drive 2 hours and 45 minutes with little more than 24 hours notice. Especially for pals I’ve known forever. And that’s exactly how I ended up on a boat floating just off the shores of Lake Michigan, with the Navy Pier to our right, waiting to capture one of the sweetest proposals I’ve ever witnessed.

My CycleBar class was wrapping up one morning when I felt my watch buzz on my arm. One of my childhood friends had texted me, and all my watched showed me was “Hi I’m reaching out to see if you have any photography contacts in the Chicago area! I’m planning on…”

A true cliff hanger let me tell you. After a quick stretch I bolted out of the room to grab my phone

“I’m planning on proposing to Taylor tomorrow evening and our photographer just backed out this morning. If you have anyone you know who you would suggest reaching out to, I’d really appreciate it if you could pass that along to me!”

If you know me, serendipity and spontaneity are my favorite things. So, I said “Where and when?? I can be there!” To which he replied:

The next day I scurried down to Chicago, which I do quite frequently, and arrived at the dock with plenty of time to hop on the boat. The boat was tied up off the North Shore of Chicago and captained by Knockout Charters (who you should absolutely look up if you’re thinking about a Chicago Proposal because they were a blast and a half to work with).

Want to see this Chicago Proposal go down on video?

Check out the reel I made from this epic evening on my Instagram!

Chicago Boat Proposal

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imagery by Mo Speer Photography | site design by foil & Ink