Santa is back on The Ledge, 103 floors above the Loop, and he's brought deep-dish pizza and a gingerbread version of the Chicago skyline with him. Holidays @ Skydeck! has returned to Willis Tower and runs through January 4, 2027, transforming the observation deck and lobby into a seasonal attraction stacked with photo ops, live performances and family dining.
Santa Takes Over the Skydeck
Santa Photo Sessions run daily from Saturday through December 24, with no sessions on Thanksgiving Day, according to theskydeck.com. Twice during the run, on December 5 and December 12, Santa will greet guests directly on The Ledge — the glass box that juts out 103 floors above the city — from 10 a.m. to 1 p.m. Photos with Santa carry varying dates, times and locations throughout the season and come with an additional fee, per the same source.
As Shaw Local reports, the celebration also includes thousands of twinkling lights, oversized ornaments and a holiday-themed Skydeck Express L train replica scattered throughout the lower-level Chicago Museum and observation deck. The outlet notes the event blends live music and festive dining with the photo ops that have become a Skydeck holiday staple.
A Gingerbread Skyline in the Wacker Drive Lobby
The season's centerpiece is a larger-than-life gingerbread display depicting Chicago's skyline, set up in Willis Tower's Wacker Drive lobby. The display was created by Chicago chef Chris Teixeira and pastry chef Miko Kaw Hok Uy, according to a release distributed via PR Newswire. The display is anticipated to be up from November 13 through January 4, per theskydeck.com, running the same length as the broader holiday program.
Skydeck's own guide to visiting Chicago in December describes the transformation in detail: the event decorates the lower-level Chicago Museum and observation deck with holiday lights and décor while adding photo opportunities, seasonal entertainment and Santa visits, according to Skydeck's visitor page.
Deep-Dish Lunches and a Nutcracker Night
Holiday Pie in the Sky family lunches are scheduled for Saturday, December 5, and Saturday, December 19, with seating at noon on the 99th floor and Santa stopping by tables, per theskydeck.com. The lunches feature Giordano's deep-dish pizza, peppermint cheesecake, a kids' menu, gingerbread decorating and holiday movies, according to the PR Newswire release.
December 5 also brings an evening event pairing Italian dining with live performances of Ballet 5:8's “Beyond the Nutcracker,” the release states. It's one of several add-on experiences layered onto the standard holiday programming this season.
Elf Cameos, School Performances and a Holiday Market
Buddy the Elf is scheduled to visit Skydeck on December 8, though the exact time has not yet been announced, per theskydeck.com. The Willis Tower Holiday Market runs December 8 through 10, with an added evening session on Thursday, December 10, from 4 to 6 p.m., the same source notes.
Local youth groups take the stage throughout the month: Chicago's Merit School of Music performs strings on December 9 and 16, Mitchell Elementary School Choir sings on December 11, and Choose Chicago Dance on Broadway performs December 12, according to the PR Newswire release.
Pajama Jam Closes Out the Run
Guests who show up in holiday pajamas from December 21 through 26 can claim a complimentary 6-by-8-inch printed photo on The Ledge, per theskydeck.com. Randy Stancik, general manager of Skydeck Chicago, said the attraction aims to make each visit memorable and to give guests new ways to enjoy the landmark together, according to the PR Newswire release. Full event details and ticket information are available at theskydeck.com/holidays-at-skydeck.
