More About Santa’s Splashy Arrival Marks the Start of the Holiday Season at Navy Pier

Dive into the holiday season with Santa’s highly anticipated return to Navy Pier on Sunday, Nov. 22. “The Big Guy” will make his splashy entrance aboard the Seadog speedboat, operated by City Cruises, arriving at Navy Pier’s South Dock at 12 p.m. He will then lead the way for guests to enjoy the magic of the holiday season at Harry Caray’s Navy Pier with brunch and photo ops in the cozy setting of the Lakefront Lodge winter pop-up from 12 p.m. to 3 p.m.

Fresh from his appearance at The Wintrust Magnificent Mile Lights Festival, Santa will trade in his sleigh for the Seadog by City Cruises and sail to Navy Pier to usher in the holiday season. Sleigh bells in hand, Santa will arrive on the bow of the Seadog speedboat and be welcomed by the Chicago Fire Department. Upon docking, Santa will greet waiting children eager to celebrate the holiday season and, escorted by the famous Shannon Rovers bagpipers performing holiday classics, lead the way to Harry Caray’s.

All are welcome to the free arrival festivities and Santa’s procession along the Pier. For those hoping to stay for brunch and take photos with Santa, reservations are strongly encouraged and can be made via the Santa’s Arrival event page on the Harry Caray’s website.

Harry Caray’s and Navy Pier will be brimming with holiday spirit all season, offering a full lineup of festive events and experiences. Check out all the holiday happenings at Harry Caray’s Navy Pier and get ready for the return of Wintrust Winter WonderFest at Navy Pier! Santa Photo Experiences are also available beginning Nov. 23. Reservations are recommended and can be made at whereissanta.com. Walk-up visits are welcome as availability allows.

Date & Time

November 22, 2026
12:00pm - 3:00pm

Location

City Cruises
600 E Grand Ave.
Chicago, IL 60611

Contact Info

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