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 Tavern 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 Tavern. 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 Tavern for brunch, photo ops, and live holiday music in the Lakefront Lodge pop-up.
City Cruises Chicago delivers a diverse range of offerings on Lake Michigan and the Chicago River, including dining cruises, sightseeing tours, and exhilarating speedboat thrill rides. Enjoy year-round dining options with three distinct experiences: Signature, featuring a lively chef-prepared buffet; Premier, offering an elegant three-course meal served with table service; and Premier Plus, an elevated three-course dining experience of utmost sophistication. Dining cruises are complemented by dynamic DJ entertainment and dancing, along with unbeatable city skyline views. Looking to celebrate the holiday season? Celebrate with City Cruises' festive dining cruises on Lake Michigan and the Chicago River. Enjoy Thanksgiving Day dinner on November 28 with a delicious feast and live entertainment. For Christmas Eve and Christmas Day on December 24 and 25, experience the yacht’s interior beautifully decorated for the holiday, along with chef-prepared meals, DJ-spun holiday music, and breathtaking city views. Ring in the New Year on December 31 with a 21+ dinner cruise featuring an all-inclusive package, an open bar, and a prime view of Navy Pier fireworks at midnight. On New Year's Eve and New Year's Day, enjoy daytime brunch cruises that are perfect for the whole family, or celebrate 2025 with friends paired with bottomless mimosas and scenic views of iconic landmarks. All cruises offer fresh, chef-prepared food and unique holiday experiences. For tickets and more information, visit citycruises.com/chicago.
Escape to a festive, alpine-inspired oasis without ever leaving the city. From November through February, the atrium and patio of Harry Caray’s Tavern transform into the Lakefront Lodge—a cozy winter retreat overlooking downtown Chicago and the icy expanse of Lake Michigan. With warm leather seating, a glowing fireplace, and rustic holiday décor, Lakefront Lodge offers the perfect setting for seasonal celebrations, corporate events, and intimate gatherings. Just outside the lodge, guests can book their own Private Curling Rink + Heated Igloo, or plan a fun game night with Harry’s Winter Warming Hut featuring jumbo games and private fire pits. Guests can customize their experience with a variety of booking options and add-on’s. For more, information visit harrycarays.com/lakefront-lodge.
Located on Lake Michigan, Navy Pier is the most visited destination in the Midwest, stretching more than six city blocks and welcoming nearly 9 million annual guests. Originally opened in 1916 as a shipping and recreation facility, this Chicago landmark showcases over 50 acres of parks, restaurants, attractions, retail shops, sightseeing and dining cruise boats, exposition facilities, and more. The Pier celebrated its 100th anniversary in 2016 with the unveiling of the Centennial Wheel, Polk Bros Park, and Peoples Energy Welcome Pavilion. Today, Navy Pier continues to usher in its second century with ongoing redevelopment efforts including the 223-room Sable hotel, the all-transient Navy Pier Marina, and thrilling new attractions such as Flyover Chicago. The Pier is proud to present free programming designed to inspire and engage communities across the city and globe, including the #1 Fireworks display in the nation. For more information, visit NavyPier.org
