Hiking & Trekking


CHICAGO · ILLINOIS

Best Hiking & Trekking In Chicago

The best of Chicago.

The 2 best hiking & trekking in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.

2 Best Hiking & Trekking In Chicago

Chicago-Style Holiday Hike: Festive Food and Walking Tour - Where the tour starts: 410 N Michigan Ave and the quick hop to the holiday core
Chicago, Food, Food & Culinary Tours, Food & Drink, Hiking & Trekking, Tour Reviews, Tours, Walking Tours

Chicago-Style Holiday Hike: Festive Food and Walking Tour

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1.Chicago-Style Holiday Hike: Festive Food and Walking Tour

Chicago holiday food and sights on foot. Small-group 3-hour hike with Christkindlmarket, Millennium Park skating, and classics like deep dish.

Most Popular★ 5.0

“I had an amazing time on this tour! Jamal was my tour guide. He was so nice and had great information about the restaurants and the city. I tried a lot of food I wouldn't have gotten on my own, and was able to see a lot of the city in only 3 hours. My…”

68 reviewsFrom $84.99by Bobby's Bike Hike - Chicago

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Fright Hike: Chicago Halloween Bike Tour - Stop-by-Stop: Streeterville, the John Hancock Center, and the Big-Sky Scares
Bike Tours, Chicago, Cycling Tours, Hiking & Trekking, Tour Reviews, Tours

Fright Hike: Chicago Halloween Bike Tour

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2.Fright Hike: Chicago Halloween Bike Tour

Chicago Halloween bike tour with included bike and helmet, a 3-hour night ride, and spooky stories at iconic sites.

★ 5.0

“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.”

7 reviewsFrom $54.99by Bobby's Bike Hike - Chicago

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