Festivals, Fairs & Special Events
Santa Sails the Seadog to Harry Caray’s Navy Pier November 22, 2026
Kick off the holiday season by welcoming Santa as he makes his grand entrance by boat on the iconic Seadog, operated by City Cruises, before heading to Harry Caray’s Navy Pier for festive brunch specials and photo ops in the cozy setting of the Lakefront Lodge pop-up!
Fresh from his appearance at the Wintrust Magnificent Mile Lights Festival, Santa will trade in his sleigh for the Seadog and sail to Navy Pier for a festive brunch at Harry Caray’s Navy Pier. Sleighbells in hand, Santa will arrive on the bow of the Seadog by City Cruises, sailing from the east end of the Pier toward the dock, greeted by one of the Chicago Fireboats from the Chicago Fire Department’s. Upon docking, Santa will greet waiting children and lead the way to Harry Caray’s Navy Pier for brunch and photo ops in the Lakefront Lodge pop-up.
TIMELINE:
- 11:45 AM | Guest are invited to gather at the Seadog Ticket Booth on Navy Pier’s South Dock around 11:45am
- 12:00 PM | Santa will arrive aboard the Seadog, greet the crowd, and lead the way to Harry Caray’s
- 12:15 PM – 3:00 PM | Brunch with Santa at Harry Caray’s Navy Pier
Reservations are strongly recommended for those wishing to attend the Brunch with Santa at Harry Caray’s and take photos with Santa.
