Holiday Hike Chicago-Style: Festive Food & Walking tour

13 Ratings
  • Live Guide
  • Instant Confirmation
  • E-Ticket
  • 3 hr

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3-hour guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for tours by bike and on foot. You’ll get to sample the Windy City’s favorite winter treats; including a slice of deep dish pizza, hot apple cider or cocoa, German bratwurst, and the original chocolate brownie recipe. Add a VIP cocktail to boot. Our entertaining guides will get your holiday spirit primed with plenty of food and knowledge. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the fabulous Christmas window displays at the original Marshall Field’s department store, Chicago's city Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market. No other tour offers such an all-encompassing experience of Chicago during the holidays!

Itinerary Details

This is a typical itinerary for this product

Stop At: Millennium Park

Meet your guide at 11:30 am at the world-famous Giordano's Pizzeria, where you will taste Chicago's unique and delectable stuffed pizza to kick off your holiday wonderland walking tour. Visit Millennium Park and gaze over the large outdoor ice-skating rink, flanked by the some of the most iconic buildings on the Chicago skyline. Watch hundreds of skaters twirl as they enjoy the free attraction. See the city’s official Christmas tree, loaded with spectacular ornaments and lights.

Duration: 1 hour

Stop At: Palmer House Hilton Historic Lobby

Next, stroll down State Street where the lights, decorations and window displays dazzle. Throughout your tour, you'll make stops for a variety of tasty treats, including a brownie sample at the Palmer House Hotel, where the chocolatey treat was invented! While inside the historic building, your guide shows you the magnificent interior architecture of this grand old hotel, where many famous guests have stayed since it opened in 1875.

Duration: 15 minutes

Stop At: Macy's on State Street

Enjoy the Holiday decor

Duration: 10 minutes

Stop At: Daley Bicentennial Plaza

Enjoy Christkindlmarkt in Chicago

Duration: 20 minutes

Stop At: Cloud Gate

Iconic Chicago attraction

Duration: 5 minutes

Stop At: Jay Pritzker Pavilion

Gorgeous open air amphitheater

Duration: 5 minutes

Pass By: The Art Institute of Chicago

Amazing collections
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