1.Style Holiday Hike: Festive Food and Walking Tour

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

A small-group Chicago holiday walking tour with German Christkindlmarket stops, Millennium Park skating views, and classic food tastings.

“Hi, I had Lilian for our group leader. I know I didn’t spell her name right but she was wonderful. I loved hearing about the history and everything of Chicago. I have been to Chicago in 2008 but had not taken this tour before obviously cause this Read more”

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2.Fright Hike: Chicago Halloween Bike Tour

★★★★★★★★★★5.0 · 7 reviews · from $54Best value

Pedal through Chicago on a Halloween bike tour with bikes and helmets included, guided ghost stories, and spooky stops from Streeterville to Lake Michigan.

“We had a blast. Our guide, Jamal, was informative and entertaining at every stop. It was so cool riding through the city at night. In addition, the equipment is clearly well cared which was so nice. Highly recommend if you’re looking for something different to do.”

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