Santa Sails the Seadog to Harry Caray's Tavern on Navy Pier

Sun Nov 23, 2025
12:00pm to 3:00pm CT
Age: All Ages
Location:
Harry Caray's Tavern Navy Pier

Dive into the holiday season with Santa’s highly anticipated return to Navy Pier on Sunday, November 23. Fresh from his appearance at The Wintrust Magnificent Mile Lights Festival, Santa will trade in his sleigh for the Seadog by City Cruises and set sail for Navy Pier.  “The Big Guy” will make his splashy entrance standing on the bow of the speedboat with sleighbells in hand, arriving at Navy Pier’s South Dock at 12 p.m. to be welcomed by a cheerful crowd gathered on the Pier and a bagpiper performing holiday classics. After greeting waiting children, he will lead guests to Harry Caray’s Tavern to continue the holiday magic with festive brunch specials and photo ops in the cozy Lakefront Lodge winter pop-up from 12 p.m. to 3 p.m.

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 Tavern website.

For more information visit harrycarays.com/lsail-sails-to-navypier

** Activity dates/times are subject to change. Please click through to the activity website to verify.