4 Chicago Christmas Tours to Book Before December

1.Style Holiday Hike: Festive Food and Walking Tour

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

Join Bobby’s Bike Hike at 11:30 a.m. for a three-hour winter walk through central Chicago. You’ll see Millennium Park, Cloud Gate, State Street, and Christkindlmarket while sampling deep-dish pizza, a Chicago-style hot dog or Italian beef, Palmer House brownies, and holiday cider. Guides such as Mickey, Brooke, Julia, and Lillian lead groups of up to 15.

“Loved the option to have a beer tasting from the local brewery and our tour guide was awesome. The food was delicious and the pizza from Lou Malnati’s pizzeria was the best deep dish we’ve ever had.”

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2.The Christmas Tree Crawl Experience Chicago at the Holidays

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

Walk about 1.5 miles through downtown Chicago with a local guide, visiting beautifully decorated interiors and outdoor holiday sights. Guides such as Hillary, Scott, and Heath bring stories about Chicago, Santa, Rudolph, and Christmas traditions to life. The tour includes holiday sweets and ends near the Christkindlmarket.

“Our tour guide was very knowledgeable and made the tour fun! He even walked us back to the Christkrindlmarket afterwards!”

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3.Christmas Eve Lake Michigan Gourmet Dinner Cruise

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

Board the Odyssey Lake Michigan at Navy Pier for a 2.5-hour Christmas Eve cruise with a private table, plated three-course dinner, DJ entertainment, and views of Willis Tower and Navy Pier. Semi-formal dress is encouraged. Coffee, hot tea, and iced tea are included, while cocktails and other alcoholic drinks cost extra.

“Improved- food is hot not cold… soda was very flat and syruppy Not sat near the door -everyone kept opening and shutting the door - it was cold. I wore my puffer jacket for the meal Many songs were in Spanish”

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

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

Spend New Year’s Eve aboard a City Cruises vessel departing from Navy Pier at 9:30 p.m. You’ll get a freshly prepared buffet, live DJ music, indoor and outdoor viewing areas, Lake Michigan views, fireworks if weather allows, and a Champagne toast at midnight. Smart casual dress is required, and the cruise returns to its starting point.

“Horrible check-in instructing and meeting point. Security was awful, but the servers and everything were fine. The issue was to get into a bout”

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