7 Chicago Holiday Tours Worth an Afternoon

1.Style Holiday Hike: Festive Food and Walking Tour

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

Walk central Chicago with a local guide, from Millennium Park’s skating rink and Christmas tree to the Christkindlmarket and State Street displays. The three-hour tour includes food tastes such as deep-dish pizza and the Palmer House brownie, plus hot cider or cocoa. Groups are capped at 15; a three-sample craft beer upgrade costs extra.

“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

Walk about 1.5 miles through downtown Chicago with a local guide, seeing festive hotel and building interiors, outdoor decorations and the city Christmas tree. Guides have included Hillary, Scott and Heath. Expect Christmas stories, a couple of holiday sweets and a finish at the Palmer House, near Christkindlmarket.

“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.Holiday Walking Tour: Underground Chicago via the Pedway

★★★★★★★★★★5.0 · 27 reviews · 3 hours (approx.) · from $65

In a small group of up to 10, follow a local guide through Chicago’s underground Pedway and aboveground landmarks, with an included L train ride. The three-hour walk starts at Swissotel Chicago at 10 a.m. and ends at Cloud Gate. Guides such as lifelong Chicago resident Tom bring local stories and can tailor the walk to your interests.

“Tom was very knowledgeable and personable. He tailored the tour to meet our needs. I highly recommend his tour.”

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4.Guided Holiday Walking Tour and Food Sampling

★★★★★★★★★★4.8 · 18 reviews · from $80

Spend three hours walking Chicago’s Loop holiday route with an English-speaking guide. See Millennium Park’s Christmas tree and rink, State Street lights, Macy’s displays, and Christkindlmarket, with food tastings and hot apple cider along the way. Past guides Jamal and Jeff earned praise for their local history and holiday spirit, but your guide may differ.

“All the historical information about the city of Chicago. It was very interesting.”

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5.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, a three-course plated dinner, and DJ entertainment. Watch for views of Willis Tower and Navy Pier from the indoor dining areas or open-air decks. The menu offers turkey, salmon, steak, or gnocchi.

“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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6.Chicago Seasonal Stroll Walking Tour of Holiday Attractions

★★★★★★★★★★5.0 · 5 reviews · 2 hours (approx.) · from $44

Join a small group of up to 15 for a two-hour, English-language walk from Petterino’s to the Wrigley Building. Expect Christkindlmarket entry access, downtown holiday sights, and stories about Chicago’s architecture and traditions. Guides Gabe, Fran, and Josie have led the tour, though your guide may vary.

“This seasonal waking tour was great and informative very nice at Christmas time. I enjoyed the walk with Fran our tour guide. She was amazing and gave us a fun experience.”

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7.Private Holiday City Tour

★★★★★★★★★★5.0 · 3 reviews · 3 hours (approx.)

Take a private holiday drive through Chicago, with a licensed guide and driver, pickup at your downtown location, and stops at the Magnificent Mile, the Loop, Solidarity Drive and Lincoln Park. Matt and Vick have guided and driven one outing, but your assigned team may differ. The tour lasts about three hours and costs $499 for up to four people.

“Matt and Vick were AMAZING!! The diversity, knowledge, and understanding was one of a kind and know I couldn't find it anywhere else. It was chilly out today but the vehicle was warm and comfortable. The uniqueness of Chicago which makes this city so monumental and the truth inside the bean! We are so happy we took those tour and blessed Matt and Vick were our tour guides and driver!”

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