Willis Tower Private Event Space · Chicago
The 99th Floor Proposal
A private floor, a path of rose petals, and the entire city of Chicago below.
Plan Your ProposalProposal Photography · Willis Tower Chicago
When the Skydeck Isn't Enough
Most people who propose at Willis Tower do it on the Skydeck — surrounded by other tourists, jostling for space in the glass Ledge boxes, checking the clock before their allotted time runs out. It's memorable. But Mike wanted something else entirely.
He had heard about a previous proposal I photographed for Carlos Frias, the food critic for the Miami Herald, who proposed to his girlfriend on the Willis Tower Skydeck. That session had made the rounds. Mike tracked me down, told me he wanted to rent the entire 99th floor private event space, and asked if I could help him coordinate it.
We built something neither of us had photographed before. And the results show it.
A Path of Rose Petals. An Empty Floor. The Whole City.
The 99th floor private event space at Willis Tower isn't the Skydeck. It's a full event floor — 360-degree panoramic windows, 300-guest capacity, no crowds, no time limits, no strangers watching.
We arranged a path of rose petals leading directly to the floor-to-ceiling windows overlooking downtown Chicago. Tiffany had no idea where they were going. Mike told her they had dinner reservations. By the time she understood what was happening, she was surrounded by the city and the only thing left to do was say yes.
I was already positioned. She never saw me until after.
Then We Took the City.
The proposal was always going to be epic. What happened after is what separates a gallery from a story.
Once the moment landed, we went to the streets. The Board of Trade building. Under the el tracks. On the el platform itself. Downtown Chicago at that hour, with those two, in that light.
It's the kind of session that happens when a couple is still running on adrenaline from the biggest moment of their lives. The emotion is raw, the joy is unguarded, and you forget entirely that there's a camera there. That's when I do my best work.
He had heard about a previous proposal I photographed at Willis Tower and tracked me down. We built something neither of us had done before.
Jeremy Glickstein
What to Know About the Willis Tower 99th Floor
The Space
The 99th floor private event space seats 50 to 300 guests and accommodates up to 400 for receptions. For a proposal, it becomes something different entirely: a private floor with panoramic 360-degree windows and no audience except the city itself. Contact Willis Tower directly at sales@theskydeck.com to inquire about proposal accommodations.
Versus the Skydeck
The Skydeck (103rd floor) is the public observation deck. The 99th floor is the private event space. The Skydeck offers The Ledge glass boxes but shares the space with tourists during public hours. The 99th floor can be reserved exclusively, giving you complete privacy, no time limit, and full control of the environment.
Photographer Access
Professional photographers are accommodated at both the Skydeck and the private event space. For the 99th floor, coordinate access through the events team in advance. I have photographed proposals at both levels of the building and can advise on positioning, timing, and the logistics of staying hidden until the moment.
After the Proposal
Downtown Chicago is one of the best backdrops in the world for post-proposal portraits. From the building, we can walk to the Board of Trade, the el tracks on Wabash, the Riverwalk, or any number of locations within minutes. Building this into your session plan turns a proposal into a full story.
The Willis Tower 99th floor proposal is not the standard approach. It requires coordination, advance booking with the venue, and a photographer who has navigated the building before. I have photographed proposals at multiple levels of Willis Tower and can help you plan the timing, the setup, and the street session that follows.
If you're considering this kind of proposal, the most important thing to do is start early. The private event space books up. Golden hour windows are limited. And the best proposals I've photographed here happened because someone planned three months out, not three weeks.
Questions About Willis Tower Proposals
Can you propose on the 99th floor of Willis Tower?
Yes. The 99th floor is Willis Tower's private event space and can be reserved for proposals and special occasions. Contact the Skydeck events team at sales@theskydeck.com to discuss availability and options. The space accommodates anything from an intimate private proposal to a larger gathering. The building staff is experienced with proposals and can help coordinate timing and logistics.
What is the difference between the Skydeck and the 99th floor?
The Skydeck is the public observation deck on the 103rd floor, featuring The Ledge glass boxes. It is open to the public during regular hours and shared with other visitors. The 99th floor is a private event space that can be reserved exclusively, giving you full control of the environment, no time constraints, and complete privacy for the proposal moment.
Can I bring a photographer to Willis Tower for a proposal?
Yes. Willis Tower accommodates professional photographers for both the public Skydeck and the private event space. For the 99th floor, coordinate photographer access through the events team when you book the space. For the Skydeck during public hours, a professional photographer can blend in with other visitors and position in advance. I have photographed proposals at both locations and can advise on the best approach for your specific plan.
What is the best time of day to propose at Willis Tower?
Sunset is the strongest option. The light through the floor-to-ceiling windows turns golden in the hour before the sun drops, and the city lights begin to emerge as the sky darkens. For the 99th floor private space, this window gives you warm interior light and a dramatic backdrop simultaneously. For the Skydeck, weekday evenings during shoulder season reduce crowd pressure significantly.
What happens after the proposal at Willis Tower?
The best sessions don't end at the building. Downtown Chicago is one of the most photogenic environments in the country and is directly outside the door. We can walk to the Board of Trade, the el tracks on Wabash Avenue, the Chicago Riverwalk, or any number of locations within a few minutes. The adrenaline from the proposal moment makes the post-proposal portrait session some of the most natural and emotional work I photograph. Building this into the plan from the beginning produces a complete gallery rather than a single captured moment.
How far in advance should I book a Willis Tower proposal photographer?
For a 99th floor private space proposal, I recommend starting three to four months out. The venue books up, golden hour windows are specific, and coordinating photographer access with venue logistics takes time to do well. I can accommodate last-minute proposals on the Skydeck with as little as 48 hours notice when my calendar allows, but private venue proposals benefit significantly from early planning.
"Jeremy worked with my fiance and planned a surprise proposal for me on the 99th floor of the Willis Tower. Not only is his work amazing, he really was a true gem to work with. Jeremy is professional, kind, patient (huge plus for someone like me haha), and just fun! He also gave us the finished edited photos early, and included a few extras. Thank you, Jeremy!"Tiffany Sabev — Google Review
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