Skydeck Chicago's annual Holidays @ Skydeck! event returns November 13 through January 4, layering food-and-beverage programming, live performances, and themed activations across Willis Tower's 103-story venue — a model that other large-format hospitality destinations have increasingly adopted to drive repeat visitation during the winter season.

The F&B Programming

Food operators and hospitality teams will note the event's deliberate use of dining as a destination driver. Holiday lunches on the 99th floor on December 5 and December 19 feature Giordano's deep-dish pizza, peppermint cheesecake, a children's menu, and gingerbread decorating alongside Santa appearances and holiday films. The December 5 evening session escalates to an exclusive Italian dining experience paired with live performances by Ballet 5:8's Beyond the Nutcracker — a format that blends ticketed F&B with performing arts, a pairing gaining traction across upscale hospitality venues nationwide.

The gingerbread centerpiece — a large-scale depiction of the Chicago skyline installed in Willis Tower's Wacker Drive lobby — was created by Chicago chef Chris Teixeira and pastry chef Miko Kaw Hok Uy, giving the display culinary credibility beyond décor.

Venue as Retail and Entertainment Hub

Skydeck Chicago is positioning Willis Tower's broader footprint as more than an observation attraction. A Holiday Market at Catalog, the tower's dining and retail destination, runs December 8–10, with extended hours on December 10. Live performances from Chicago's Merit School of Music, Mitchell Elementary School Choir, and Choose Chicago Dance on Broadway are scheduled across multiple December dates, keeping foot traffic active through the month.

"We want every visit to Skydeck to be a memorable experience, especially during the holidays," said Randy Stancik, General Manager of Skydeck Chicago. "We give visitors new ways to enjoy this iconic Chicago landmark together, whether it's their first visit or an annual tradition."

The strategy reflects a broader shift in how landmark venues are monetizing seasonal windows — stacking experiential retail, curated dining, and entertainment into a single destination visit rather than relying on the core attraction alone. For foodservice and restaurant operators tracking experiential dining trends, the Skydeck model illustrates how F&B programming can serve as both a revenue layer and a loyalty mechanism within non-traditional hospitality venues.

Additional activations include a Buddy the Elf character appearance on December 8, professional photos with Santa from November 14 through December 24 (available on The Ledge for an additional fee), and a Holiday Pajama Jam running December 21–26 that offers guests in holiday pajamas a complimentary printed photo.

Written by Michael Politz, Author of Guide to Restaurant Success: The Proven Process for Starting Any Restaurant Business From Scratch to Success (ISBN: 978-1-119-66896-1), Founder of Food & Beverage Magazine, the leading online magazine and resource in the industry. Designer of the Bluetooth logo and recognized in Entrepreneur Magazine's "Top 40 Under 40" for founding American Wholesale Floral, Politz is also the Co-founder of the Proof Awards and the CPG Awards and a partner in numerous consumer brands across the food and beverage sector.