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Festivals, Fairs & Special Events

Santa Sails the Seadog to Harry Caray’s Tavern

Kick off the holiday season by welcoming Santa as he makes his grand entrance aboard the iconic Seadog, operated by City Cruises, before heading to Harry Caray’s Tavern for brunch, photo ops, live music, and the Grand Opening of it’s winter pop-up, the Lakefront Lodge!

Fresh off his appearance at the Wintrust Magnificent Mile Lights Festival, Santa will trade in his sled for the Seadog by City Cruises and sail to Navy Pier for Brunch with Santa at Harry Caray’s Tavern’s new pop-up, the Lakefront Lodge. Watch him make his grand entrance aboard the Seadog by City Cruises at noon as the Chicago Fire Department welcomes him into the harbor with their impressive water cannons. Upon his arrival at Navy Pier, he’ll head to Harry Caray’s, for photo ops, delicious brunch bites, and live holiday music by local musician, Kathleen Lane.

  • Santa Arrives | 12pm
  • Brunch with Santa* | 12pm-3pm
  • Live Holiday Music | 12:30pm-3pm

*Reservations strongly encouraged


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