4 Chicago Christmas Tours Worth Booking

1.Style Holiday Hike: Festive Food and Walking Tour

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

Join a guide such as Mickey, Brooke, Julia, or Lillian for a three-hour Chicago holiday walk with deep-dish pizza, a Palmer House brownie, a Chicago-style hot dog or Italian beef, cider, Millennium Park sights, State Street decorations, and Christkindlmarket access.

“This was mine and my husband's first time visiting Chicago together. I came to visit the Christkindlmarket, and I chose the Holiday Hike tour for its combination of food tastings and tour of the city. The food was full servings so quite filling after viRead more”

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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 such as Hillary, Scott, or Heath. Visit festive hotel interiors, see Marshall Field’s windows, Chicago’s official tree, and Christkindlmarket, while enjoying holiday sweets and stories about Christmas traditions.

“Hit some great spots. Tour guide was very knowledgeable about the history. Considering the cold temperatures, never got cold. Good combination of being outdoors & indoors.”

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3.Christmas Eve Lake Michigan Gourmet Dinner Cruise

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

Spend 2.5 hours aboard Odyssey Lake Michigan on Christmas Eve. You’ll enjoy a private table, three-course plated dinner, DJ music, hot drinks, and 360-degree views of Chicago landmarks including Navy Pier and Willis Tower. Semi-formal dress is encouraged, and alcohol costs extra.

“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

Set sail from Navy Pier at 9:30 pm for a three-hour New Year’s Eve cruise on Lake Michigan. You’ll have a freshly prepared buffet, live DJ, indoor and outdoor viewing areas, Chicago skyline views, and a midnight Champagne toast. Check-in can take patience, so arrive early.

“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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