Adventure Collective
Holiday Food & Walking Tour with Bobby's Bike Hike Chicago - Chicago

Holiday Food & Walking Tour with Bobby's Bike Hike Chicago

Chicagoeasy

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.

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.

Frequently Asked Questions

Recommended Gear

Insulated Jacket

Essential

Keeps you warm during the outdoor portions of the tour amid Chicago’s winter chill.

winter specific

Waterproof Boots

Essential

Protects feet from slush and snow while maintaining comfort on city streets.

winter specific

Gloves

Essential

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.

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