Holiday Hike: Season Sampling Chicago Walking & Food Tour

Get into the holiday spirit on Bobby’s Bike Hike’s Holiday Hike, a festive walking and food tour of downtown Chicago. This three-hour tour combines the best of Chicago’s holiday cheer with delicious food samples, iconic landmarks, and festive sights. Explore the Magnificent Mile’s holiday lights, the Millennium Park Christmas Tree, and the German-inspired Christkindlmarket—all while enjoying local favorites like deep dish pizza and Chicago-style hot dogs.

Your journey begins at Lou Malnati’s Pizzeria, a Chicago staple, where you’ll indulge in the city’s famous deep dish pizza, known for its cheesy goodness and rich history. After a slice, your guide will lead you through downtown’s holiday highlights, including the beautiful Christmas tree at the Wrigley Building, the Chicago Theatre’s Christmas marquee, and the bustling Riverwalk.

The fun continues with visits to iconic locations like Millennium Park, home to the Cloud Gate (aka "The Bean") and the city’s Christmas Tree. Along the way, you’ll sample more local treats, including Italian beef sandwiches and Chicago brownies at the historic Palmer House hotel. The tour concludes with a visit to the Christkindlmarket, where you’ll savor German-inspired holiday foods and explore unique gifts from around the world.

This tour is perfect for families, friends, and anyone looking to experience the magic of Chicago during the holiday season. Whether you're indulging in festive treats or simply soaking in the holiday cheer, the Holiday Hike offers an unforgettable way to explore the city’s winter wonderland.