I CAN NOT wait to show you all this surprise proposal that took place at Milton Lee Olive Park in Chicago! Anthony planned out the perfect proposal day for his now fiancée Bre and I am so so excited that I was able to be a part of it. These two are such a fun couple and we had such an amazing day together! So without further ado check out their surprise Chicago proposal!

The Ruse

Bre and Anthony were in Chicago for the day celebrating Bre’s 30th birthday. Anthony made up the story that he had booked a photographer to take some portraits of Bre to celebrate her birthday, so after their lunch they headed to Navy Pier where I met them for some portrait photos. Only doing portraits before we moved onto Milton Lee Olive Park for their proposal really sold the idea that I was only there for the portraits, and Bre was none the wiser!

Proposal at Milton Lee Olive Park

Once we made it to Milton Lee Olive Park we started taking some more photos while I waited for Anthony’s signal for the proposal. We decided on a game for his cue where I would tell him to say three of his favorite things about Bre as a prompt for photos, and he’d use that to start his proposal. Bre has the biggest smile, so watching their proposal and her face light up when Anthony popped the question was such a cool experience! After Anthony had made his move and we got some photos of the two of them celebrating this moment we walked around the park for some more portraits before moving on to the final part of their day.

On the Water

As a last surprise for their proposal day, Anthony had one of his buddies who has a speed boat come and pick us up after we were done at Milton Lee Olive Park to take us out on the water. This was an incredible way to finish off their proposal day, sipping champagne out on the waters of Lake Michigan and celebrating the love they share for one another. It was seriously such an incredible experience all around!

I am seriously SO obsessed with Bre and Anthony’s proposal at Milton Lee Olive Park. Anthony planned the perfect day for Bre and him to celebrate their love and now they get to start the exciting process of planning their wedding together! I LOVE proposals, so if you’re planning one of your own and are looking for a photographer to capture your epic moment, I’m your girl! Head to my contact page and let’s start planning!