Megan and Bryan

Wedding Proposal Ideas in Sky Deck - Chicago, IL

How We Met

Bryan and I met our freshman year of high school in Palm Beach, Florida 12 years ago. We didn’t have any classes together at the time, but had some common friends and ending up sitting together during lunch periods. He was a funny, charismatic, class-clown type who always had holes in his jeans and played guitar (read: lady killerrr). I was a little quieter back then. I definitely had my own creative style (so thankful social media wasn’t as big back then) and was closet nerd (minus the closet part).

We dated for over a year in high school, but it didn’t quite work out, and we parted ways before leaving high school. While he went to the University of Miami in Coral Gables and studied business, I attended the University of Florida in Gainesville and studied engineering. We dated other people in college and would check in with each other now and then, but honestly, I figured I wouldn’t see much of Bryan again.

As my senior year was coming to a close, I started interviewing for jobs and luckily ended up with multiple offers. One of my top choices was back in South Florida, while the others were great opportunities in different states and different industries. Part of me wanted to move somewhere different, but in the end I decided to take the job in South Florida. So, I packed up all my things and moved back in early 2012. Shortly after I moved back, I received a random text from a number I hadn’t seen pop up on my phone in years.

Turns out, Bryan had moved back to the area too, and decided to reach out. Things haven’t been the same since! We went on our second first date shortly after that text. I started the night by tripping in my new wedges when he picked me up, but we ended the night catching up and laughing like nothing had changed. Something had changed, however. I like to think both grew up a little, and grew into our own. Luckily for us, we grew into two people even more compatible than our high school selves could dream of!

how they asked

Megan’s Version: I can say I was completely surprised the night Bryan proposed. He told me it was a business meeting and described the clients in detail, even down to what type of dog they had! We even sat on separate sides of the airplane on the flight there (not what you would expect for a romantic trip). I did think it was odd how many Jack Daniels and Coke’s he consumed on the flight there, but he had said these were big clients and he was nervous! In fact, throughout the day, he kept saying how nervous he was for tonight.


We went through what he would say during lunch at Lou Malnatis (yum), and I kept telling him it would be fine, that he was great at this type of thing. Little did I know I was encouraging him to relax about proposing to me later that night! We stayed in a beautiful hotel, and when the time came to go to the Willis Tower to meet these “clients”, we made our way there via taxi. When we got there we went through a different entrance and it was pretty empty, which I thought was odd, but the front desk staff seemed to know these “clients” and exactly where we were going. After a bit of waiting because the “clients” were running late, I was getting hungry and wondering what the holdup was. Finally, just as I was about to complain, someone came to bring us to the elevator.

He kept up the charade pretty well throughout the long elevator ride, talking about the clients and why they were late; the Sky Deck is on the 103rd floor. When the door opened, I expected to see a restaurant or meeting space, but instead a staff member handed me a beautiful bouquet of white roses. I saw rose pedals arranged in an aisle leading us to the Sky Deck and heard our favorite song playing on the violin. As I walked I finally put it together. Everything felt like a dream – I was truly on cloud nine, and almost high enough up to be in the actual clouds! He got down on one knee, with the city lights surrounding us, and asked me to marry him.


Of course, I said yes!


Bryan’s Version: It took me 6 months to plan the proposal, pick the ring, and coordinate everything to make it great. The first thing I did was make a list of our favorite places in the US. We’d been to Chicago two years prior, we both really enjoyed the city, and I decided that would be the perfect place. Next, I started looking for the perfect spot in the city to pop the question. I thought about the peer, parks, and restaurants but nothing felt right. Megan made me feel like I was on top of the world and I wanted her to know that when I asked. That gave me an idea.

I started looking into roof tops in the city. None of the rooftops did it for me, but I remembered that the Willis Tower had the Sky Deck – a glass box that hangs off of the building on the 103rd floor. How cool would it be to ask in the tallest building in the city with only glass beneath our feet? We would be suspended in the moment and suspended in midair. That felt perfect.

I reached out to the staff at the Sky Deck and they told me that they did proposals all the time there and it would be very easy to plan mine. I asked if I could do a private proposal, and that’s where the idea started to fall apart. The Sky Deck does proposals during regular business hours. You pay for a regular admission ticket, tell them your names, and they reserve a box for you. It’s not private by any means though, and knowing Megan, that was a deal breaker. I knew she wanted the moment to feel private and she wouldn’t want a crowd watching her when I asked. I asked the staff at the Sky Deck if there was any way to rent the floor. They had never done that before and it took some convincing to make it happen. Long story short, they made an exception and worked with me to get up to the Sky Deck, just after public hours, for 30 minutes.

I planned everything with security downstairs, I had a particular entrance I had to use, I had a code word to tell the front desk, it was fool-proof. I also hired a photographer, a videographer, and a violinist to play our favorite song during the proposal. The staff knew their names and were ready to get them upstairs. We had a 30-minute window to make this happen. If I was late to the building, they couldn’t guarantee the floor would be empty, so everything had to go perfectly. I couldn’t speak with any of the vendors the day of, so I had my friend coordinate with them to make sure they got there on time and everything went well.

I told Megan we were going to Chicago for a business meeting and we were scheduled to meet the clients at 8:30 at the Willis Tower and then head for drinks afterwards. We barely left our hotel in time to get there. Megan couldn’t decide whether it was cold enough to wear tights with her dress. I couldn’t say anything, but I kept insisting we couldn’t be late to the “meeting”. We got to Willis Tower right at 8:30 and a ton of things were flooding my mind.


What was I going to say, what if the people at the front desk say something, so many things could go wrong.

We had a few hiccups, but thankfully Megan didn’t put it together that I was going to ask her to marry me that night. We got into the elevator on the way up and everything immediately felt so real. I was completely in the moment. As we got closer to the top, I could hear the violin music getting louder and louder. The doors opened up and there was a bouquet of flowers waiting for Megan just like we planned. My heart rate slowed down as I realized everything turned out perfect. Megan seemed surprised and confused at first and then she put it together. We walked down the aisle of rose pedals to the glass Sky Deck waiting for us.


I told her exactly how I felt from the heart, got down on one knee, and asked her to marry me.


She said yes.



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Special Thanks

Thom Anthony
Shawna Flowers
Blue Nile