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

410 N. Michigan Ave.Chicago, IL 60601
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Holiday Hike: Season Sampling Food & Walking Tour is not currently available.

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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!

1 or more people

Good To Know

  • Walk 1.25 miles across the city and see the city decorated for the holidays along the way.
  • Tour duration: approximately 2.5 hours long.
  • Tours available daily at 11:30 am daily through Dec. 24th.
  • Includes food and beverage samples along the way.


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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Holiday Hike: Season Sampling Food & Walking Tour is located at 410 N. Michigan Ave.Chicago, IL 60601
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Frequently Asked Questions about Holiday Hike: Season Sampling Food & Walking Tour

How long and strenuous is the walking tour?
The tour covers 1.25 miles in 2.5 hours at a relaxed pace. Our 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. Please note your request for food accommodations when booking your tour in the “Have Special Needs?” field.

Can you accommodate food allergies or vegetarians on your food tours?
We CAN provide food substitutions for vegetarians on ALL tours. Gluten-free substitutions are available on certain tours. While we try our very best to accommodate food allergies, we cannot guarantee certain avoidance from various food allergies. We would encourage you to ask questions along the way and see if our guide might recommend a substitution.

May I bring my dog on this tour?
Sorry, pets are not allowed on any of our tours.

Will there be breaks for restrooms?
Our walking tours start at various locations around the City and while we do our best to accommodate restrooms at the start of your tour, we do highly recommend using the restroom prior to arrival to your tour. We will have restroom stops built into each walking tour. For our food and walking tours, all of the restaurants we visit will have restrooms to use.

Do you offer water on your tours?
We do not provide water on our tours due to the fact that they all originate from locations outside of our headquarters. Please plan ahead and bring water with you. For our culinary, restaurant and food tours our restaurant partners will provide water free of charge.

Do you have a stroller I can use for my child?
No stroller, no problem! We rent strollers out for daily use, multi-daily use. But most of our walking tours do not originate from our bike shop. You will want to make arrangements in advance to rent and pick up your stroller. Please note that our tour guides many times meet the group directly in the neighborhood covered on the tour, without stopping at the bike shop, so we cannot deliver strollers to you.

Are your tours ADA accessible?
All of our walking tours at the present moment do allow for ADA compliant and wheelchair accessible. But please note that sometimes our restaurants change and we cannot guarantee every restaurant will not include stairs of some sort which might make things difficult. A majority of our stops should be ADA compliant.

What should I wear? What should I bring?
We recommend you bring small items such as an ID, credit card and cash (to tip the guide), cell phone, and camera. We suggest tennis shoes and comfortable, loose-fitting clothes that are appropriate for the weather conditions on the day of your tour. We strongly suggest you wear layers, particularly in spring and fall. Many of our tours are downtown, close to Lake Michigan, which is one of the largest lakes in the world and can alter the temperature quickly based on the direction of the wind.

How much walking is involved?
Not more than you can handle! The pace is usually good for everyone. We’ve rated each tour-level so that you can pick the right tour for you. We do stop at various points of interest and attractions so that you can have a brief rest while our tour guides explain the history of Chicago in a way that brings the stories to life. While you want to make sure the distance we cover is suitable for you, remember that we will never be walking continuously for that amount of time. We will have 6-8 stops mixed in along the route for resting periods and to learn about Chicago. Please note that with some of our walking tours there are some stairs that we navigate during the tour.

Are tours offered in bad weather?
We run most of our tours in any type of weather. Walking tours run year round as they are less dependent on stable weather for their operation. During the nicer months, we use the beautiful outdoor promenades for our walking tours. And during inclement weather, we can duck down and use Chicago’s unique underground pedway system to get from point to point. Just remember to always dress for the weather.  Because our walking tours do not leave from our headquarter location, we do not provide rain ponchos should a pop-up shower occurs

Are guide gratuities included in the price?
The tour price does not include gratuities in the cost of our tours. If you had a great time, gratuities are accepted by our tour guides.