Holiday Food & Walking Tour with Bobby's Bike Hike Chicago
Difficulty
easy
Duration
3 hours
Fitness Level
Suitable for most fitness levels; involves walking at a relaxed pace over urban sidewalks.
Overview
Step into Chicago’s holiday glow with Bobby’s Bike Hike’s festive walking tour. Taste the city’s deep dish pizza, soak up Christkindlmarket’s charm, and stroll beneath dazzling lights on this three-hour winter outing.
Holiday Hike: Season Sampling Food & Walking Tour
Starting at $79.99 | 3 Hours | See and taste how Chicago celebrates the holidays!
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Adventure Photos
About This Adventure
Embark on Bobby’s Holiday Hike, a delightful three-hour walking tour through Chicago's festive winter wonderland! Savor deep dish pizza, explore the enchanting Christkindlmarket, and enjoy the dazzling lights of the Magnificent Mile. Perfect for families and friends, this tour offers a unique way to celebrate the holiday season together.
Rates
Prices starting at $79.99
Duration
3 Hours
About
Taste your way through the holiday season on this food and beverage walking tour! This holiday-themed tour begins at the end of November and runs through Christmas Eve. Bobby’s Holiday Hike is a great way to experience all that Chicago has to offer during the winter holidays in a single afternoon stroll! See the lights of the Magnificent Mile, enjoy a warm and filling deep dish pizza, experience the German-inspired festivities of Christkindlmarket, and toast to a joyful season over a hot chocolate! VIP beer/cocktail upgrade available for an additional price. This three-hour Chicago holiday tour is perfect for families, friends, holiday parties, and anyone looking to celebrate the season in an exciting new way. All Food & Beverage Samples included in Ticket Price.
Adventure Tips
Dress in Warm, Layered Clothing
Chicago winters can be bitter; layering helps you stay comfortable while walking through outdoor markets and city streets.
Wear Comfortable, Waterproof Footwear
Sidewalks may be snowy or slushy—sturdy shoes with good traction will keep your footing secure during the three-hour tour.
Bring a Portable Hand Warmer
Hand warmers can enhance comfort during outdoor stops, especially near the riverfront or crowded market spaces.
Reserve in Advance
This popular seasonal tour requires a minimum of two guests and sells out quickly during holidays, so book early to secure your spot.
Local Insights
Wildlife
- Urban squirrels adapted to colder seasons
- Winter migratory birds seen around Lake Michigan's shoreline
History
Christkindlmarket started in Chicago in 1996, based on the traditional German Christmas market that dates back centuries, enriching the city's festive culture.
Conservation
The City of Chicago promotes sustainable holiday events by encouraging waste reduction and supporting local vendors within Christkindlmarket.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Insulated Jacket
Keeps you warm during the outdoor portions of the tour amid Chicago’s winter chill.
winter specific
Waterproof Boots
Protects feet from slush and snow while maintaining comfort on city streets.
winter specific
Gloves
Essential for keeping hands warm during stops at outdoor markets and walking segments.
winter specific
Small Backpack
Useful for carrying extra layers, camera, or any souvenirs picked up along the way.