Surprise Proposal Rooftop Chicago

Surprise Proposal on a Rooftop Building in Chicago

Dylan Today, I have for you Dylan’s surprise proposal story! He was planning for several weeks to do it on the rooftop of their apartament building in Chicago. They do have an amazing view towards downtown Chicago. Dylan and Madi have been together for 8 years. 

I asked Dylan how he coordinated or decided on what place to propose? 

“8 years ago, I asked her out during the encore song ‘Better Together’ at Jack Johnson. On our anniversary, I gifted Madison tickets to Jack Johnson because he was coming back to Chicago at the end of the month. After seeing her reaction to the gift, I knew it was the perfect time to pop the question. I started reaching out to her sisters and family for ideas, got a ring at Fey & Co and then I just waited. I wanted to ask at the concert but her sister said no!  Her sister Lexi had the idea of proposing on the rooftop. Many people helped coordinate the moment while keeping it a secret”

Dylan was prepared with everything: champagne, rose petals and of course! ” The ring!” The only thing that did not work out was the rose petals as the wind blew them away in seconds before Madi made her entrance. 

surprise proposal
she said yes
the ring


the ring


After the surprise proposal on the rooftop with the Chicago skyline in the background we decided to go across the street in Lincoln Park to take few portraits just to mark the moment.


Lincoln park
honeycomb portrait
Lincoln Park view
ice-cream truck

Any tips on how to prepare for the proposal?
“Have an idea of what you want to say but don’t script it. Just let it happen!”

Any tips that you have about preparing your fiancé for the proposal? What did you tell her, how did you get her to cooperate, what did you do or what would you have done differently?

“Use her family to help and have a “plan” that corresponds to the way you think she would want to dress.”

It was a pleasure capturing this wonderful surprise proposal on the rooftop in Chicago!! Looking forward to capturing many more happy moments with Dylan and Madi!! 



Here is another Surprise Proposal in Chicago

This Post Has 2 Comments

  1. Great photographs of Madi and Dylan’s surprise proposal! Love every picture!!!

    1. Thank you Sandra!! It was so beautiful to see the proposal live and I am glad that I was able to show the story!

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