Milton Lee Olive Park Surprise Proposal | Bre + Anthony

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!

Girl smiles during a photo session in a striped jump suit at Navy Pier

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!

Man kisses his girlfriend on the cheek while they hug with the sun shining bright in the background
Man kisses his girlfriend while they hug with the sun shining bright in the background

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.

fiancés holding one another second before their proposal at Milton Lee Olive Park
Man proposes to his girlfriend on a summer day at Milton Lee Olive Park.
Man proposes to his girlfriend on a summer day at Milton Lee Olive Park.
Fiancés kissing just after the girl says yes to her proposal at Milton Lee Olive Park in Chicago.
Fiancés just after the girl says yes to her proposal at Milton Lee Olive Park in Chicago.
Fiancé puts a ring on his future bride standing in front of the Chicago skyline.
Fiancés kiss just after their proposal standing on the lakefront in Chicago
Fiancés stand holding each others hands just after proposing in Milton Lee Olive Park
Fiancés hug after their surprise proposal at Milton Lee Olive Park
Fiancés kiss after their surprise proposal at Milton Lee Olive Park
Fiancés admire their engagement ring just after their proposal at Milton Lee Olive Park
Fiancés snuggle in tight and hug on the lake front in Chicago during their engagement session at Milton Lee Olive Park
Fiancés snuggle in tight and hug on the lake front in Chicago during their engagement session at Milton Lee Olive Park
Fiancés snuggle in tight and hug on the lake front in Chicago during their engagement session at Milton Lee Olive Park
A wide photo of fiancés snuggle in tight and hug on the lake front in Chicago during their engagement session at Milton Lee Olive Park with the skyline in the background
Fiancés snuggle in tight and hug on the lake front in Chicago during their engagement session at Milton Lee Olive Park
Fiancés snuggle in tight and hug on the lake front in Chicago during their engagement session at Milton Lee Olive Park with the Chicago skyline in focus
Fiancés snuggle in tight and hug on the lake front in Chicago during their engagement session at Milton Lee Olive Park, this photo is a close up of the engagement ring.
Fiancés snuggle in tight and hug on the lake front in Chicago during their engagement session at Milton Lee Olive Park
Fiancés snuggle in tight and hug on the lake front in Chicago during their engagement session at Milton Lee Olive Park
Fiancés dance the lake front in Chicago just after their surprise proposal at Milton Lee Olive Park
Fiancés dance the lake front in Chicago just after their surprise proposal at Milton Lee Olive Park

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!

Fiancés sit on a small speedboat with champagne on lake Michigan during their engagement session in Chicago
Fiancés sit kissing on a small speedboat with champagne on lake Michigan during their engagement session in Chicago
Fiancés shout at the camera while holding a bottle of champagne celebrating their Chicago proposal on a boat on lake Michigan
Fiancés hug and look at the camera while holding a bottle of champagne celebrating their Chicago proposal on a boat on lake Michigan
Fiancés smile and look at the camera while celebrating their Chicago proposal on a boat on lake Michigan
Fiancés pour champagne on a boat out on lake Michigan celebrating their engagement
Fiancés sip champagne and admire their engagement ring on a boat out on lake Michigan celebrating their engagement
Fiancés snuggle in tight on a boat admiring the Chicago skyline
Fiancés snuggle in tight on a boat admiring the Chicago skyline
Fiancés kiss and hold each other tight on a boat admiring the Chicago skyline during their engagement session
Fiancés hold each other tight on a boat admiring the Chicago skyline during their engagement session
Fiancés hold each other tight on a boat admiring the Chicago skyline during their engagement session
Fiancés kiss and hold each other tight on a boat in Chicago with a lighthouse in the background during their engagement session
Fiancés hold each other tight on a boat in Chicago with a lighthouse in the background during their engagement session
The Chicago skyline at sunset overlooking Lake Michigan

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!

A view of the Chicago skyline from a speedboat on Lake Michigan
  1. […] the planning process! If you need some inspiration for your Chicago Proposal, check out this one at Milton Lee Olive Park I photographed. And if you’re ready to book a photographer for your proposal head over to my […]

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About Jayde 

Docu-torial Photographer

I'm a Chicago wedding photographer with a passion for people, candid moments, authenticity, and golden hour. I document weddings with a ferocity for the real moments that matter on a wedding day: the moments you lived with the people you love. With 200+ weddings under my belt, I use my expertise to guide my clients to feel comfortable and confident so their images feel like them. 

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