Chicago-Style Holiday Hike: Festive Food and Walking Tour
TICKET PRICES STARTING FROM
Taxes and fees will be calculated at checkout
Overview
There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Bike Hike & Food Tours, internationally recognized for food tour quality, presents our Holiday Hike, a 3hr guided Walking & Chicago Food Tour through top holiday attractions. You’ll get to sample the Windy City’s favorite winter treats; including a slice of deepdish pizza, Chicago-style hot dog, Italian Beef, chocolate brownie, & hot apple cider. Upon arrival, you can add a VIP holiday drink pairing($19.99/person). Our entertaining, local guides will get your holiday spirit primed with plenty of food & stories. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the Christmas window displays at the original Marshall Field’s store, the Chicago Christmas tree, ice skating rink at Millennium Park, & VIP entrance to the legendary Christkindlmarket, a traditional German Christmas Market. No other tour offers such an all-inclusive experience of Chicago during the holidays!
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
- Chicago’s towering Christmas tree sparkles with color & warmth, a glowing centerpiece of the season.
- Skip Christkindlmarket lines and enjoy VIP Christmas cider before doing your own Holiday shopping.
- 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.
- Macy’s holiday windows dazzle with bright scenes and festive charm, a true Chicago winter tradition.
- Millennium Park’s ice rink glows w/ holiday energy as skaters glide under Chicago’s bright skyline.
- The original brownie—rich, warm, and fudgy, a sweet holiday treat that melts into pure joy.
- Led by a local English-speaking guide sharing Chicago’s festive flavors, stories, and holiday cheer.
- Michigan Avenue glows with bright holiday lights, turning the city into a magical winter walkway.
- 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)you can purchase this option upon arrival for $19.99/person
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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