Holiday Hike: Season Sampling Walking & Food Tour Tickets in Chicago, IL

There’s nothing more magical than downtown Chicago during the holiday season. Experience all of the excitement and cheer with Bobby’s Holiday Hike! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, whose walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Traveler Magazine. Bobby’s Holiday Hike is a three-hour guided walking and food tour through the Chicago Loop. You’ll get to sample the Windy City’s favorite winter eats including a slice of deep-dish pizza, hot apple cider, craft beer, German bratwurst, and a chocolate brownie; learning all about Chicago’s history with these dishes along the way. You’ll see the fabulous Christmas window displays at the original Marshall Field’s department store, the annual municipal Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market that has been setting up shop in Chicago for years. No other tour offers such an all-encompassing experience of Chicago during the holidays!

- Price includes food, drinks, a guide, knowledge, and lots of laughs.
- Guide gratuity not included, 15-20% is customary and appreciated!
- Be sure to wear comfy clothes for Chicago’s dynamic weather trends!
- All ages are welcome, come have fun with the whole family!

Please note: While you may register as a solo rider on our tours, there is a 3 person minimum for this particular tour to go out. If we do not hit this threshold 2 hours before tour time we may contact you to reschedule or possibly cancel the tour with a full refund.