How Matt proposed to Emma on the Willis Tower Skydeck Ledge at sunset. What it took to pull it off, and where we went next.
Emma had been waiting a little bit for her ring. A quick scroll through her social media revealed a post using Raye’s “Where Is My Husband” as the song, posted just a few days before Matt actually proposed. She thought it was coming. She just did not know when. Or where. Or how.
What she did not know is that Matt and I had been communicating for months about a Chicago Skydeck proposal that would happen at sunset on the 103rd floor of the Willis Tower. And that a chance encounter at a bar in Iowa had brought her to this moment.
Why Willis Tower, and why the sunset
Matt wanted to propose above the city with the sunset lighting up Chicago behind them. The Willis Tower Skydeck offers private rental opportunities after closing time, which is the option most couples looking for a Willis Tower engagement moment default to. But those rentals happen after the observation deck closes, which means no sunset. No golden hour light. No skyline glowing warm behind the ring.
Matt wanted the sun. So we skipped the private rental and did it a different way.
He purchased two Skydeck tickets, plus a third for me, and we timed the whole thing to arrive on the observation deck as the sun was low in the western sky. Just before closing. Just as the light was doing what it does best.
A private rental gets you the view. A ticketed visit at the right hour gets you the light. For a Chicago Skydeck proposal, the light is part of the show.
The hiding game
Emma and Matt shared a romantic dinner, enjoying Chicago’s downtown restaurant scene. Then they Ubered over to the Willis Tower. I met them at the Skydeck. Well, I say I met them. What actually happened is that I waited outside the elevators, watched them arrive, and then started a game of following them without being seen.
This is harder than it sounds. The Skydeck observation floor is not a large space. You cannot exactly hide behind a pillar for twenty minutes without being noticed. What makes it possible is that everyone at the Skydeck is holding a camera and taking pictures. A photographer with a lens looks like every other tourist. I blended in.
I followed them into the room where you wait in line for your ninety seconds on The Ledge. I had corresponded with an employee at the Skydeck ahead of time who volunteered to help me out. He spotted them right away. Matt in a tailored suit. Emma in an elegant yellow dress. They were dressed for something.
They took their place in line. Matt and I waited with anticipation and, I will admit, a little bit of nerves. \
THE CONSTRAINT- You get ninety seconds on The Ledge.
This is the thing most couples planning a Willis Tower Skydeck proposal do not know about. There is a time limit on The Ledge. Ninety seconds per group. That means the ring, the words, the yes, the tears, the hug, and the first photographs all technically need to happen inside that window. The good news: the Skydeck staff is understanding when a proposal is unfolding. If you wanted more photos you can go back to the end of the line for another ninety-second turn if you want more portraits. Plan for ninety seconds, hope for a little grace. That is why the coordination matters so much on a proposal like this.
The moment on The Ledge
After some time in line, they finally reached the front. It was their turn. Emma stepped out onto the glass Ledge, 1,353 feet above the sidewalk below, with the entire city of Chicago spread out beneath her feet.
I came out of nowhere from the other side of the room where I had been hiding. I raised my camera. And Matt got down on one knee.
Emma had been waiting for her ring, but the moment still hit her like she had not seen it coming at all. Gratitude, love, disbelief, all rushed in at once. The city glowed underneath them. The sun sat low behind the skyline. Matt shared his words. Emma got a little emotional. She said yes.
And then all the folks around us erupted in cheers. Strangers who had been waiting in line behind them realized what they had just witnessed and started applauding. We probably went over the ninety seconds. I don’t think anyone minded. That is the kind of flexibility you get when the whole room is rooting for you.
We captured the moment, the ring, the reaction, the embrace, and a few of the wider skyline images that make a Chicago Skydeck proposal so unlike any other proposal location in the city.
Down to the Riverwalk
When it was all done, Matt and Emma decided to extend their shoot into the night. They wanted a few more portraits to remember the day, and since they were visiting from the Pacific Northwest, it felt fitting to take advantage of Chicago’s most photogenic outdoor setting. So we headed down to the Riverwalk.
The light had shifted by the time we got there. The sun was fully down. The city lights had come on. The Wrigley Building glowed white above the river. The bridges lit up in warm amber. Every reflection on the water made the whole scene feel almost cinematic. Like something out of a movie.
The Riverwalk is one of the most photogenic engagement locations in Chicago, and it works so well at night because the reflections do half the work for you. The river becomes a mirror. Every building becomes a light source. Every corner has a different angle to work with.
Emma kept bursting into laughter and smiles between poses. She was just so happy. Every few minutes she would look at her hand, see the ring, and start smiling all over again. Matt would grin. I would keep shooting.
We were able to capture a wide variety of pictures in a short amount of time because the Riverwalk is just that photogenic. It gave us a completely different feeling from the Skydeck images. The Skydeck was the moment. The Riverwalk was the celebration after.
Planning your own Skydeck proposal?
If you are thinking about a Chicago Skydeck proposal at Willis Tower, a few things are worth knowing from someone who has now pulled one off.
Decide between private rental and ticketed visit early. Private rentals give you the entire observation deck to yourselves but only after closing time, which means no sunset (during the summer). Ticketed visits give you access during operating hours, which means you can catch the light, but you share the space with other visitors. Matt chose the light. Both options are valid depending on what matters most to you.
You get ninety seconds on The Ledge per turn. This is the single most important logistical fact about a Skydeck proposal. The good news is that the Skydeck staff most likely will give a little extra grace during actual proposals, and you can also go back to the end of the line for another turn if you want more portraits. But plan for ninety seconds, hope for a little more, and know that whatever you get on The Ledge, it will be worth it. Your photographer needs to know exactly where they will be standing, exactly what the moment will look like, and exactly which shots to prioritize during those first ninety seconds.
Time your arrival for the light, not the crowds. Late afternoon on weekdays is quieter than weekends. Sunset times vary throughout the year, so time this carefully.
Plan for extended coverage. If you are already spending on a Skydeck ticket and coordinating months in advance, add extra coverage after so you can get more portraits somewhere beautiful. The Riverwalk is a natural next stop. It is a short drive from Willis Tower, it photographs beautifully at any hour, and it lets your new fiancée actually breathe and enjoy the moment after the intensity of The Ledge.
If you want to see other Chicago proposal locations worth considering, I put together a guide to the best Chicago proposal locations with sixteen spots ranging from rooftops to gardens to skyline overlooks.
PLANNING YOUR CHICAGO PROPOSAL?
Let’s plan something they will remember forever.
I’m Kenny Nakai, a Chicago wedding photographer who has been documenting proposals across the city since 2007. From the Willis Tower Skydeck to the Riverwalk to hidden rooftops most photographers do not know about, I help you plan, scout, and execute the surprise, and capture every second of it beautifully. See my Chicago proposal photographer service for pricing and process.
