5 Chicago Christmas Tours Worth Booking

1.Chicago-Style Holiday Hike: Festive Food and Walking Tour

★★★★★★★★★★5.0 · 68 reviews · from $84Our pick

Walk central Chicago with a local guide such as Mickey, Brooke, Julia, or Lillian, stopping for deep-dish pizza, a brownie, a Chicago hot dog or Italian beef, cider, and holiday sights. The three-hour tour is limited to 15 people and includes quick access to Christkindlmarket, Millennium Park, and State Street displays.

“We really loved this tour. Brooke was knowledgeable with great energy. Loved her! One suggestion. During holidays when kriskrindlmarket cups are available, serve last stop hot chocolate in them for people taking tour.”

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2.The Christmas Tree Crawl Experience Chicago at the Holidays

★★★★★★★★★★5.0 · 44 reviews · 2 hours (approx.) · from $35Best value

Join Inside Chicago Walking Tours for a two-hour, 1.5-mile holiday walk from Peet’s Coffee on Michigan Avenue to the Palmer House. Guides such as Hillary, Scott, and Heath mix Chicago stories with Christmas traditions, festive trees, historic interiors, treats, and stops near Christkindlmarket. Expect outdoor walking, indoor breaks, and a small group of up to 20.

“The tour guide rocked he was fun and knew a lot. He was also up beat and made the whole experience better!”

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3.Chicago: Christmas Eve Lake Michigan Gourmet Dinner Cruise

★★★★★★★★★★4.8 · 12 reviews · from $193

Spend 2.5 hours aboard Odyssey Lake Michigan on Christmas Eve, with a private table, three-course plated dinner, DJ music, and views of Navy Pier, Willis Tower, and Chicago’s skyline. You can sit indoors, step onto the open-air decks, and order cocktails while coffee, hot tea, and iced tea remain included.

“Muy divertido! La cena muy rica y el DJ genial. las vistas a la ciudad desde el lago fueron increíbles! Muy recomendable. El staff muy amable.”

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4.Chicago New Year’s Eve Buffet Dinner Cruise on Lake Michigan

★★★★★★★★★★4.0 · 11 reviews · from $273

You’ll board a City Cruises vessel at Navy Pier at 9:30 pm for about three hours of buffet dining, DJ music, dancing, and Lake Michigan fireworks. Indoor heated areas and outdoor decks give you viewing choices. Plan for smart-casual dress, a busy check-in, and possible delays if the vessel is not clearly marked.

“Tudo incrível Só não sabíamos que barco ia .não tinha Internet e o aplicativo não abria e ninguém sabia qual ir Sufoco Mas no barco foi incrível tudo maravilhoso”

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5.New Year’s Eve Plated Dinner Cruise on Lake Michigan

★★★★★★★★★★5.0 · 2 reviews · from $341

Start at Navy Pier at 9:30 pm for a four-hour New Year’s Eve cruise on Lake Michigan. Enjoy a three-course plated dinner, tableside service, city views, fireworks, onboard entertainment, and dancing. The Silver Package includes the Platinum Open Bar. This adults-only experience accepts guests age 21 and older.

“Special way to spend New Year's Eve. The city looked great from out on Lake Michigan. The food was quite good and the service was excellent.”

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