From November 24, Navy Pier in Chicago will transform into a festive holiday destination. The event kicks off with Santa arriving on the Seadog by City Cruises, following his appearance at the Wintrust Magnificent Mile Lights Festival. "Sleighbells in hand, he will make his grand entrance by boat at Noon as the Chicago Fire Department welcomes him into the harbor with an impressive water cannon salute." Santa's arrival will be followed by brunch and activities at Harry Caray’s Tavern.

Navy Pier will host Housegiving on November 27, featuring house music from artists like Bad Boy Bill and Julian Jumpin Perez. General admission is priced at $15.

The Light Up the Lake celebration begins on November 29 and runs through January 5. It includes various attractions such as ice slides, bonfires, fireworks, drone shows, and millions of lights visible from DuSable Lakeshore Drive.

Santa will be available for visits in the Family Pavilion every weekend from November 29 to December 22. Visitors can also enjoy Holiday Artisan Markets and Crafting Workshops during weekends from November 30 to January 5.

Winterland at Illuminarium offers a ticketed experience featuring snow-covered forests and festive photo backdrops from November 22 to January 5. At Harry Caray’s Tavern, guests can visit Lakefront Lodge or participate in curling activities through February.

Margaritaville Bar and Grill introduces Christmas Island with new holiday drinks and events every Saturday until December 31. The Sable Hotel’s Lirica Restaurant offers prix fixe dining experiences on Thanksgiving, Christmas Eve, and Christmas Day.

Offshore Rooftop transforms into a retro-themed snow globe setting for holiday celebrations. City Cruises Chicago provides brunches and dinners with skyline views throughout the season. Shoreline Sightseeing reintroduces its Holiday Express Water Taxi service for city travel on weekends.