Chicago-Style Holiday Hike: Festive Food and Walking Tour
TICKET PRICES STARTING FROM
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Overview
There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided walking and food tour of the city’s top seasonal attractions. You’ll sample Chicago favorites like deep-dish pizza, a Chicago-style hot dog, Italian beef, a chocolate brownie, and hot apple cider. Alcoholic beverages aren’t included, but holiday drink pairings can be added on-site. Our local guides will fill the tour with festive stories—like how Rudolph the Red-Nosed Reindeer originated in Chicago. You’ll see the classic holiday windows at the original Marshall Field’s, the Chicago Christmas tree, the Millennium Park ice rink, and enjoy VIP entry to the Christkindlmarket. No other tour offers such a complete Chicago holiday experience!
TICKET PRICES STARTING FROM
Taxes and fees will be calculated at checkout
GET TICKETSTicket Options (1) Options Available
Option(s)
Holiday Hike: Festive Chicago Food and Walking Tour
Starting from
$9.99
Ticket Information
- Mobile or paper ticket accepted
- One per booking
What's Included
- Tender Italian beef soaked in rich jus, warming you up like the perfect savory holiday comfort.
- A Chicago dog loaded with bold flavors—bright, zesty, and perfect for a festive winter bite.
- The original brownie—rich, warm, and fudgy, a sweet holiday treat that melts into pure joy.
- Led by a local English-speaking guide
- Enjoy deep dish pizza, Italian beef, a Chicago-style hot dog, brownies, hot apple cider, and festive bites that make this Chicago Food Tour a Holidays and Christmas feast of iconic city flavors.
- Hot Christkindlmarket cider—steaming, spiced, and soul-warming, the perfect festive winter sip.
- Savor Chicago-style pizza, a warm Christmas and Holidays favorite baked to perfection.
What's not Included
- $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
- Hotel pickup and drop-off
- Local drink samples can be added for a fee (Three 9oz pours)
Cancellation Policy
- For a full refund, cancel at least 24 hours before the scheduled departure time.
Additional Info
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Suitable for all physical fitness levels
- If you have dietary restrictions, please add a note in the special requirements section when booking, and email to reservations@bobbysbikehike.com after booking to confirm they can accommodate.
- Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets.
- VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+)
- TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002.
- Our groups have exclusive VIP access to locations we visit, including VIP access to Christkindlmarket.
- Operates in all weather conditions, please dress appropriately
- Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
- Chicago’s famous foods are built on grit, hard work, and the spirit of the people who shaped this city. They’re bold, hearty, and not for everyone—so come with an open mind as we savor a classic hot dog stand, deep-dish pizza, Italian beef, and the original brownie, all with a touch of Christmas-season warmth.
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