10 festive tours to book in Chicago for Christmas

Christmas is a magical time to visit Chicago. Explore markets, try local cuisine and enjoy the best views in town on amazing tours.

View of the Christkindlmarket in Chicago, Illinois

Chicago is a bustling city with plenty to do year-round, but during the holidays there’s a festive atmosphere on the streets that makes visiting even more special. Whether week or weekend visithave a merry Christmas visit to Chicago by joining a seasonal or holiday program town tour at the most wonderful time of the year.


10/10 Delicious city vacation tour

walk it chicago winter streets on a festive food and walking tour this holiday season. Travelers will visit an exterior German style market called Christkindlmarket, where they can enjoy hot cider. They’ll also stop at a local bar to sample seasonal craft beers and enjoy brownies at the Palmer House Hotel.

  • Round:
    Holiday Hike Chicago-Style: Festive Food and Walking Tour

  • Duration:
    3 hours

  • Cost:
    From US$79.99 per adult

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Related: 10 Most Picture-Worthy Places in Chicago

9/10 Chicago by Segway

Pick up the pace on a Chicago segway tour. This two-hour adventure takes travelers through Chicago’s Millennium Park to the Loop with the help of a guide. The tour also stops at Christkindlmarket in Daley Plaza. The German Christmas market is the perfect place to get into the holiday spirit.

  • Round:
    Chicago Holiday Lights Segway Tour

  • Duration:
    ~2 hours

  • Cost:
    From US$75.10 per adult

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8/10 Chicago Craft Brewery Tour

Get into the holiday spirit as you sample some of the city’s best locally brewed craft beers. This unique tour takes travelers aboard a Prohibition-inspired brewery barrel-shaped bus and transports them to area breweries with a professional guide. It is possible to visit the brewing facilities and taste the delicious craft beers.

  • Round:
    Chicago Craft Brewery Bus Tour

  • Duration:
    3 hours and 45 minutes

  • Cost:
    From US$99.60 per adult

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Related: Chicago’s Old Town Still Exists, Here’s What to Expect

7/10 Chinatown Food Tour

Warm up on a cold winter’s day in Chicago with a delicious food tour through the city’s Chinatown. Try authentic dishes like dumplings, soups, ducks and more. Learn about China’s different regional specialties and find out which drinks pair best with each type of food.

  • Round:
    Chicago Chinatown Food and Walking Tour

  • Duration:
    3 hours

  • Cost:
    From US$79.99 per adult

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6/10 Seasonal walking tour

For a simple yet informative tour of the city, embark on a walking tour of Chicago that explores top vacation attractions. A local guide will explain the vacation traditions that began here in Chicago while taking travelers around the Chicago Loop, Millennium Park and the Magnificent Mile. The tour also stops at the German Christmas market in Christkindlmarket, but does not include food or drinks.

  • Round:
    Chicago Seasonal Walking Tour of Vacation Attractions

  • Duration:
    2 hours

  • Cost:
    From US$34.99 per adult

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5/10 Chicago Food and Walking Tour

Nothing says Christmas vacation like indulging in comfort food, chocolates and pastries. Experience Chicago from a foodie’s perspective on this in-depth downtown food tour. Travelers will sample famous Chicago dishes like deep pizza and hot dogs. They will also enjoy chocolates and other treats. It is possible to upgrade the tour to include three different craft beers.

  • Round:
    Chicago Favorites Ultimate Food & Walking Tour

  • Duration:
    3 hours

  • Cost:
    From US$74.99 per adult

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4/10 Chicago Lakefront Campus and Museum Segway Tour

Explore Chicago’s “Front Yard” on an epic tour of its lakefront area and museum campus, but with a twist: by segway! The tour included training to ride the segway safely and provides a fun way to see Chicago at a fast pace during the winter. Small group sizes ensure everyone gets the segway training they need. Highlights of the tour include visiting Buckingham Fountain and the Chicago Skyline.

  • Round:
    Chicago Lakeside and Museum Campus Small-Group Tour

  • Duration:
    2 hours

  • Cost:
    From US$76.48 per adult

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3/10 Private Chicago Pub Crawl

The festive season is the perfect time to sit down in some of the city’s best pubs and get cozy with a craft beer while learning about local history. Although this private pub crawl is expensive, it is a unique experience that travelers are sure to remember. The tour takes guests back to the prohibition era of the 1920s with a tour guide in traditional costume. Travelers enjoy skip-the-line access to these local speakeasies, accessed through secret entrances. At one time they were used by gangsters and members of the mafia. Tour participants are also encouraged to come in traditional period attire.

  • Round:
    Private Chicago Speakeasy Pub Crawl with a Local Historian

  • Duration:
    3 hours

  • Cost:
    From US$880 per group

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2/10 Chicago Bike Tour

When visiting Chicago in late November or early December before the holidays, taking a bike tour is a fun way to see more of the city and its holiday decor. Travelers will travel approximately 13 miles on this tour through some of Chicago’s best neighborhoods. The trip price includes stops at two breweries, a bakery, a hot dog stand, and a pizzeria.

  • Round:
    Bikes, Bites, and Beers: Iconic Chicago Foods Bike Tour

  • Duration:
    4 hours

  • Cost:
    From US$89.99 per adult

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1/10 See Chicago from above

See the city lights set up for Christmas from a spectacular vantage point with Skydeck entry. The Skydeck is on the 103rd floor of willis tower and is the highest point in the city. There are no better place to get a panoramic view of Chicagoand it is especially magical during the holidays.

  • Round:
    Skydeck Chicago Admission Ticket

  • Duration:
    1.5-2 hours

  • Cost:
    From US$45 per adult

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