The 10th Love on The Ledge contest pairs a social-media competition with ceremonies, hospitality and a distinctive Chicago attraction experience.
Skydeck Chicago is inviting couples to compete for wedding ceremonies or vow renewals on The Ledge, the glass observation deck on the 103rd floor of Willis Tower. The 10th annual Love on The Ledge contest will give four winning couples the chance to exchange vows 1,353 feet above Chicago, positioning the attraction as both a visitor destination and a setting for a highly shareable personal milestone.
Entries require a video or image and a short explanation of why each couple wants to celebrate with Chicago as the backdrop. Submissions are being accepted through Skydeck’s Facebook and Instagram pages via an official sweepstakes form from November 11, 2025 through January 9, 2026, extending the attraction’s Valentine’s Day offer beyond a conventional visit or proposal package.
The four selected couples are scheduled to receive private, officiated 15-minute wedding ceremonies or vow renewals on February 8, 2026. The experience includes romantic florals, décor and the presence of loved ones, while a stay at Canopy by Hilton Chicago Central Loop is planned for the evening before the ceremonies, with the hotel located directly across from Willis Tower.
The package also includes paid overnight parking, professional photography, breakfast and a celebratory champagne toast after the ceremony. For Skydeck, the contest builds on an existing connection between the attraction and romantic occasions: the company says the observation deck has hosted more than 1,600 proposals, weddings and vow renewals, alongside thousands of romantic dates.
The contest also directs couples beyond The Ledge to Skydeck’s lower-level museum, an immersive Chicago-themed experience featuring photo opportunities and material focused on the city’s history, culture, cuisine and architecture. That combination gives the attraction a broader role in the occasion, turning a short ceremony into a planned hospitality and tourism experience while keeping Chicago’s skyline central to the proposition.
