The 2 Hiking & Trekking Tours in Chicago That Earn Their Price

1.Style Holiday Hike: Festive Food and Walking Tour

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

Walk central Chicago with a local guide and a group capped at 15. You’ll see Millennium Park, Cloud Gate, State Street, and Christkindlmarket while tasting deep-dish pizza, a Chicago-style hot dog or Italian beef, Palmer House brownie, and holiday cider. A three-beer upgrade is available for adults.

“We loved our tour!!! Learned so much about the city and got to eat some delicious food!! Would definitely recommend doing!! Lillian was our tour guide. She was great!!”

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2.Fright Hike: Chicago Halloween Bike Tour

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

Ride about 8 to 9 miles through Chicago after dark with a small group of up to 15. Your guide, such as Jamal or Josie, leads you from Streeterville to the Hancock Center, Iroquois Theatre, Congress Plaza, Grant Park, and Lake Michigan while bikes, helmets, and lights are provided.

“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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