Zachary + Crystal | Skydeck Proposal Willis Tower
Skydeck Chicago Proposal at Willis Tower
Is the Skydeck at Willis Tower a good location for a proposal in Chicago?
What makes the Skydeck such an iconic place to propose in Chicago?
Located on the 103rd floor of the Willis Tower, Skydeck Chicago offers one of the most breathtaking views in the city. The Skydeck has a glass floor Boxed Ledge that lets you stand over 1,300 feet above the city! This is what makes this space such an ironic and romantic place to propose. With vast skyline views, you’ll see Chicago landmarks like Millennium Park, Navy Pier, and the Chicago River, and the sprawling neighborhoods creating a stunning backdrop.
When is the best time to propose at the Skydeck?
For the best light and chance of fewer crowds, plan your proposal early in the morning, during golden hour at sunset or in the late evening when the city is lit up. When booking your reservation with the Skydeck it can be a good idea to ask them what their busy times are during the particular time of the season. Booking during off‑peak hours ensures more privacy and uninterrupted time on The Ledge.
How to Plan An Excuse For Visiting The Skydeck
How did Zach keep his Skydeck proposal a surprise?
To make the moment a total shock, Zach told Crystal he had won “free Skydeck tickets and lunch at Willis Tower” through a company raffle. He added that the restaurant had a dress code, giving them the perfect excuse to look their best.
He also booked the Skydeck Chicago proposal package, which offers reserved time on The Ledge, priority entry, and optional add ons like champagne, rose petals, or private space for a celebration. Zach even arranged a champagne toast on the 67th floor, overlooking the city. What an elegant and romantic way to end their engagement moment.
What does a proposal at the Skydeck Chicago look like?
What to expect with a proposal at the Skydeck Chicago?
As the couple stepped onto The Ledge with the glass beneath their feet and the city glowing below. Zach turned to Crystal, took her hands, and asked her to marry him. With the Chicago skyline behind and them and city below. Crystals face lit up once she realized what was happening! She immediately said yes and they embraced on top of the city.
I played the role as a staff photographer offering the couple their complimentary photo for the experience. This felt normal and seamless as they are many photo opportunities throughout.
How do photographers help capture Skydeck proposals?
Because Skydeck proposals happen quickly, having a professional photographer ensures every moment gets captured, from the surprise to the celebration. The lighting, glass reflections, and cityscape all combine to create breathtaking images.
Why the Skydeck is Perfect for Chicago Engagement Photos
What makes Skydeck photos so unique?
The Ledge glass boxes create one‑of‑a‑kind photos with the skyline below you.
Panoramic views reveal up to four states on clear days.
The modern Willis Tower architecture adds an urban and elegant aesthetic.
The 67th floor provides an intimate space for portraits and champagne moments.
Tips for the best engagement photos at the Skydeck:
Dress for the view — choose classic, neutral colors that complement the city skyline.
Avoid peak times — weekday mornings or sunset hours are ideal.
Plan a believable cover story if it’s a surprise proposal.
Coordinate with staff — they can help with timing and setup.
Hire a photographer experienced with skydeck proposals, me :)
Check the weather for clear visibility and best lighting conditions.
What Happens After the “Yes!”
How did Zach and Crystal celebrate their engagement?
After she said yes, they enjoyed a private toast overlooking the Grant Park. It was the perfect way to step away from the commotion and slow things down to take in the moment together. This really made the experience perfect. Not only did we get stunning photos on The Ledge, but we were able to get cozy moments cherishing the moment together.
What can couples do after a Skydeck proposal?
Many couples continue their night with dinner at nearby Chicago favorites like The Dearborn, LondonHouse Rooftop, or Gibsons Italia. There are so many great locations downtown to celebrate after. Another reason why the Skydeck makes for a great location!
How to Plan Your Own Skydeck Chicago Proposal
Thinking of proposing at Willis Tower? Here’s what to know:
Visit Skydeck Chicago’s official site for proposal and private event packages.
Reserve early — spots are limited, especially during weekends and holidays.
Dress to impress; the lighting and city reflections photograph beautifully in formalwear.
Schedule time for portraits after the proposal.
Pair your proposal with a dinner reservation or private celebration nearby.
Where is Skydeck Chicago located?
Willis Tower is located at 233 S. Wacker Drive, Chicago, IL 60606 — right in the Loop, close to the Chicago River and Union Station. Parking and public transportation options make it easy to access from anywhere in the city.
Congrats again!
I’ll be in touch soon with the full gallery, in the meantime enjoy these highlights!
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