Skydeck Chicago Announces 10th Annual ‘Love on The Ledge’ Contest for 2025

Skydeck Chicago, at the 103rd level of the renowned Willis Tower, is marking its 10th anniversary of love in the clouds with the return of the much-awaited Love on the Ledge contest. Pairs of lovers can now secure a unique chance to marry or get their vows renewed at a height of 1,353 feet, with Chicago’s skyline as a striking background. This love contest, which has turned out to be a part of the city’s Valentine’s Day festivities, encourages couples to share their tales to be selected for the ceremony on the iconic glass observatory.

As Skydeck Chicago marks a decade of this extraordinary tradition, the Love on The Ledge contest continues to provide an unforgettable experience for couples seeking a truly unique wedding or vow renewal. The contest is open from November 11, 2025, to January 9, 2026, allowing couples plenty of time to share their love stories through images, videos, and heartfelt explanations of why they want to celebrate their special day atop Chicago’s tallest building.

How to Enter the Contest

Entering the Love on The Ledge contest is simple. Couples are invited to submit a video or photo, accompanied by a short narrative explaining why they wish to tie the knot or renew their vows at such a distinctive location. Submissions can be made through Skydeck Chicago’s official Facebook or Instagram pages, with the winners selected by the Skydeck team. The lucky couples will receive a private, officiated 15-minute ceremony on February 8, 2026, creating memories that will last a lifetime.

A Day to Remember with Romantic Touches

The four winning couples will not only get the thrill of exchanging vows high above the city but will also enjoy a range of special treats. Each couple will be whisked away for a romantic overnight stay at the Canopy by Hilton Chicago Central Loop, located just across the street from Willis Tower, before their big day. The prize includes complimentary overnight parking, a professional photographer to capture the magical moments, a breakfast the morning of the ceremony, and a champagne toast to celebrate the union.

Skydeck Chicago’s observation deck offers stunning panoramic views that stretch up to 50 miles and four states, providing a truly awe-inspiring setting for any special occasion. Over the years, the venue has hosted more than 1,600 proposals, weddings, vow renewals, and countless romantic moments, making it one of the most sought-after destinations for couples looking to celebrate their love.

An Unmatched Chicago Experience

Beyond the ceremony itself, couples will have the opportunity to explore the Skydeck’s interactive museum, which celebrates Chicago’s rich history, culture, and architecture. Visitors can enjoy playful photo ops and discover the Windy City’s iconic landmarks in a fun and immersive environment.

For many couples, the chance to wed or renew vows at Skydeck Chicago is not just about the ceremony—it’s about the experience. The Love on The Ledge contest invites participants to be part of something special, with the city as their backdrop and the memory of a lifetime in the making.

A Romantic Tradition at Skydeck Chicago

As Skydeck Chicago celebrates a decade of love, General Manager Randy Stancik reflects on the significance of this milestone. The contest has become an annual tradition, drawing couples from all over the world who want to create unforgettable memories. With its stunning location and romantic atmosphere, Skydeck Chicago has become a symbol of love for many, and this year’s contest promises to continue that legacy.

A Perfect Valentine’s Day Celebration

Skydeck Chicago’s Love on The Ledge contest is the ultimate way to celebrate love in the heart of the city. Whether couples are planning their first wedding or renewing their vows, the chance to do so 1,353 feet above Chicago with sweeping views of the skyline is an opportunity too special to miss. With the 10th anniversary of the contest on the horizon, Skydeck Chicago promises to continue offering a unique, magical experience for couples who want to take their love to new heights.

For more details on how to enter and to learn more about this once-in-a-lifetime opportunity, visit Skydeck Chicago’s official social media pages or website.

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