Ike proposing to Emily at Milton Lee Park in Chicago Illinois

Emily + Ike’s Proposal at Milton Lee Olive Park in Chicago

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A little over a year ago, I photographed a very special proposal at Milton Lee Olive Park in Chicago. Ike asked me to photograph his proposal to my sister, Emily.

Let me get you into the feels.

Mid-October I get a text from Ike. Now this is not out of the ordinary, but I knew what the text was for. He was asking me what weekends I had free in the next few weeks. Being a wedding photographer, my free weekends in the Fall are pretty nonexistent. Thankfully, one of the weekends I was free matched up with a date Ike had in mind for a proposal. We booked our hotels and flights within a few days of deciding on a date. Now all he had do to was ask my parents for their blessing; and come up with his plan on time and where exactly he wanted to propose.

3 weeks later I got this Snapchat from Ike.

Ike telling me he got our parents approval for him to propose to Emily.

When I tell you my excitement hit a whole new level. I started crying I was so happy.

The week leading up to the trip to Chicago, I knew I had to come up with a reason I was going to be out of town and couldn’t hang out with Emily. Easy, I had a “session” in Dubuque. Traveling back home was so common for me in 2021, no one ever questioned it. My only problem, my entire family tracks each others location using an app called Life360. When I tell you this app is spot on, it knows how fast your driving and your phones battery level. If I just stopped sharing my location she would know. However, I had been having some phone issues with service going in and out, I could blame my “lack of location” on technology.

Our First and Only Roadblock

My mom, older sister, Emily, Ike and myself went out to dinner at Olive Garden a few days before the planned proposal. I asked Em what she was going to do while I was out of town for the weekend. Her response, “I picked up a shift at work.” 😳 My face should have given it away, I quickly shot Ike an ‘oh shit’ look.

Knowing Ike would handle it, we quickly changed topic. I flew into Chicago the day before so I wouldn’t be on the same flight. I checked into the Aloft Chicago Mag Mile, which was near where they used to live. Just a few blocks from Milton Lee Olive Park! They used to take their dog, Medic on walks to this park.

Proposal Day at Milton Lee Park!

Ike eventually told Em she couldn’t work on November 20th because he had plans. Of course she kept asking and had her own ideas; but once Ike told her “I haven’t even asked your parents,” she stopped asking questions. Thankfully, when she asked my mom and dad if he asked, they played along with the plan.

Proposal day started with some spilled coffee and cold temperatures. Emily once again started questioning things when Ike’s dad showed up to be their chauffeur. A few minutes into the drive to the airport, Em asked if she needed her ID where they would be going. Naturally Emily didn’t bring it with her in the midst of their chaotic morning. Jerry quickly turned the car around, raced back to their house so she could get her ID. They made their flight just in time and Ike eventually told her they were going to Chicago! Again grew Emily’s excitement and curiosity.

Emily and Ike on a surprise flight to Chicago

It’s Proposal Time!

I was told a general timeframe to be hidden out at Milton Lee park, so naturally I got there an hour early. Checking Life360 every 10 minutes to check their movement around Chicago. Once I saw they were making their way to the park, I hit a whole new level of excitement. Friends, I was shaking, I was so nervous she would spot me and I would spoil the entire thing. While I was waiting I kept going up to random families and groups of people and starting random conversations. I even met some other creatives who were there to capture a proposal that was also happening shortly after ours was planned. They offered to film Ike’s Proposal, keep reading to see the proposal in action!

About 15 minutes after they started moving near Milton Lee Park, I crouched down directly back from “the spot.”

Emily and Ike holding hands at Milton Lee Olive Park in Chicago, IL.

Ike at one point stood up and looked around to spot me and make sure I knew it was happening.

Ike giving the go ahead that he was proposing

After about 5 minutes of them sitting on a bench and enjoying the view of the city, they turned around to take a selfie. Then they got up and she started to walk away. At this moment I swear she saw me.

Thankfully Ike quickly grabbed her hand and she turned to him on one knee. From here, I will let the photos do the storytelling.

After the Proposal

Ike proposed with a beautiful custom ring from Josephs Jewelers featuring a stunning Emerald Cut Diamond. And yes, Emily did spot me but Ike didn’t give it time to register before he turned her around.

We called family, friends and then watched another proposal happen! There were two other proposals that happened nearby. After the final one, the couples had to show of the rings and say their congrats. It was so neat to watch different proposals happen; knowing each one had so much thought and planning put into them.

I joined Emily and Ike for lunch at one of their favorite restaurants, Robert’s, and said my goodbyes. I had a flight to catch.

A huge thank you to Luke Kran and Ryan Alioto for filming the proposal at Milton Lee Olive Park!

We are just a few months away for Emily and Ike’s Spring wedding. I cannot wait to continue celebrating their love!

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