Thinking about visiting Navy Pier for the holidays? Here's the packed seasonal lineup

Navy Pier Thinking about visiting Navy Pier for the holidays? Here's the packed seasonal lineup Alongside the Wintrust Winter WonderFest, the Centennial Wheel will also be open for the season, offering winter rides even on the coldest days and nights. By Matt Stefanski • Published November 7, 2026 • Updated on November 7, 2026 at 2:22 pm The holidays are approaching, and Navy Pier is going all in, with everything from an iconic festival and signature fireworks to seasonal food and drink offerings. Among the highlights is Wintrust Winter WonderFest, a festive winter playground featuring larger-than-life holiday décor, exhilarating rides, various attractions and activities for all ages. The festival, held in Navy Pier's Festival Hall, runs from Nov. 27 through Jan. 3, 2027. Stream NBC 5 for free, 24/7, wherever you are. WATCH HERE Fans of Navy Pier's signature fireworks shows will be able to watch dazzling displays light up the night sky following the Wintrust Magnificent Mile Lights Festival on Saturday, Nov. 21. The festivities continue Sunday with a special visit from Santa, who will arrive aboard City Cruises' Seadog before heading to Harry Caray's Lakefront Lodge, according to a news release. Beginning the following day, Monday, Nov. 23, guests will be able to pose for photos with Santa as they share their Christmas wishes. One of Navy Pier's signature experiences, the Centennial Wheel, will also be open for the season, offering winter rides even on the coldest days and nights. And that's just a sample of the jam-packed holiday itinerary. Local Chicago Bears 3 hours ago 10-year-old Bears fan podcasters attend their first game CTA 4 hours ago CTA bus driver kidnapping renews concerns over transit worker safety Additional events and holiday offerings include: Housegiving - The ultimate pre-Thanksgiving celebration begins at 5 p.m. Wednesday, Nov. 25. Hosted by Shannon “Skip” Syas and DJ Threejay, the event features emerging talent and legendary artists, including DJ Flipside, DJ Nehpets, Mickey Oliver, DJ Metro, Tim Schommer, Myra, Jade and more. Chicago's Christmas Tree Ship - The U.S. Coast Guard will mark the 27th anniversary voyage of the Coast Guard Cutter Mackinaw, Chicago's Christmas Tree Ship, when it arrives Dec. 5, carrying more than 1,000 fresh-cut Christmas trees for local families. Chicago Children’s Museum - As part of Winter Weeks of Play from Dec. 21 through Jan. 3, visitors can celebrate the season with a dance party, make a royal crown and get cozy in a winter castle. Guests can also create scented play-dough sculptures during the Holiday Dough workshop, which runs Dec. 16 through Jan. 4. Chicago Shakespeare Theater - The Tony Award-winning theater will celebrate its 40th anniversary with performances of William Shakespeare's "The Winter's Tale" and "A Midsummer Night's Dream" throughout November and December. When it comes to food and drinks, there's no shortage of festive options. On Dec. 13, Holiday Sip Around the Pier will give guests 21 and older a chance to visit participating restaurants and bars for holiday cocktail specials and signature sips. Additional winter experiences will be offered by establishments including Harry Caray's at Navy Pier, Margaritaville, Offshore Rooftop, PAK's on the Pier and TE'AMO Boba & Dessert Café. This article tagged under: Navy Pier