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

Bobby's Bike Hike410 N. Michigan Ave.Chicago, IL 60601
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There’s nothing more magical than Chicago during the holiday season. Embark on a walking tour through Chicago’s most festive neighborhoods and restaurants. Sample the city’s best pizza while marveling at sights and decorations along the Magnificent Mile, strolling through Christkindlmarket, and sipping on the Windy City’s best craft beer. It’ll be a holiday season unlike any other!

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Good To Know

from Ashley, one of our Chicago Travel Experts
  • Sample on famous Chicago food and enjoy the festive downtown Christmas décor. Walk for about 1.25 miles for approximately 2.5 to 3 hours.
  • Meet your tour guide at Lou Malnati's Pizzeria inside the Wrigley Building.
  • Please arrive 15 minutes before the scheduled tour time.
  • Sample famous Chicago-style hotdogs, deep-dish pizza, beef sandwiches, hot apple ciders, and more!
  • Visit Christkindlmarket, Millennium Park Christmas tree, Magnificent Mile lights, and Marshall Field's holiday window displays.
  • This family-friendly tour runs snow, rain, or shine, so dress in weather-appropriate, comfortable attire and walking shoes.
  • Please bring a valid photo ID, bottled water, credit card, cash to tip the guide, mobile phone, and camera for pictures.
  • Tour prices include all food samples and cider. Upgrade to VIP beer add-on ticket for three (3) craft beer samples. For ages 21+ only!


from Holiday Hike: Season Sampling Food & Walking Tour
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.

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Frequently Asked Questions about Holiday Hike: Season Sampling Food & Walking Tour

Where does the tour depart from?

The Holiday Hike food and walking tour departs from Lou Malnati’s Pizzeria, inside the Wrigley Building at 410 N. Michigan Ave., Chicago, IL 60611.

How long and strenuous is the walking tour?

The tour covers 1.25 miles in 2.5 to 3 hours at a relaxed pace. The guides will lead you from attraction to attraction, stopping to give you insight into this amazing city. At many landmarks, there will be places to sit down during the presentation.

Is there a vegetarians option?

Vegetarian substitutes are provided on the tour. If you or any member of your party has dietary restrictions, please make a note in the "Have Special Needs?" section above when booking your reservation.

What should I wear?

Please wear comfortable, weather-appropriate clothing and shoes for walking.

What should I bring?

Please bring a valid government-issued ID (especially for adults), bottled water, credit card, cash to tip the guide, mobile phone, and camera to capture delightful Christmas decor!

Will there be breaks for restrooms?

Yes, all of the restaurants you visit will have restrooms to use. But best to use the restroom before your scheduled tour to have more time to enjoy the festive sights and food!

What happens if it rains or snows?

The tour runs snow, rain, or shine. If it gets canceled due to inclement weather, management will reach out to reschedule or offer a full refund.

Is the tour recommended for children?

Yes, absolutely! The tour is a perfect activity for families, friends, holiday parties, and anyone wanting to celebrate the holiday season in a new, exciting way!

May I bring my dog on this tour?

Sorry, pets are not allowed on the tour.