What You Will Do
There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for their tours. You’ll get to sample the Windy City’s favorite winter treats; including a slice of deep dish pizza, Chicago-style hot dog, Italian Beef, chocolate brownie, and hot apple cider. Upon arrival, you can add a VIP holiday craft beer package for $19.99/person. 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 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-inclusive experience of Chicago during the holidays!
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Itinerary
Meeting Point
Departure Point: Lou Malnati's Pizzeria - Wrigley Building
Directions: Please note that the entrance is located on the Northside of the Wrigley Building - ground level. Your guide will be wearing a Bobby's Bike Hike shirt and paddle.
1
Christkindlemarket
10 minutes
Enjoy a hot cider at this outdoor german christmas market
2
Palmer House Hilton Historic Lobby
15 minutes
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.
3
Macy's on State Street
10 minutes
Enjoy the Holiday decor
4
Millennium Park
1 hour
Get a full tour of 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.
5
Cloud Gate
5 minutes
Iconic Chicago attraction
6
Jay Pritzker Pavilion
5 minutes
Gorgeous open air amphitheater
7
Daley Bicentennial Plaza
20 minutes
Enjoy Christkindlmarkt in Chicago
8
Chicago Christmas Tree
5 minutes
Visit Chicago's Christmas Tree
9
Wrigley Building
5 minutes
Visit one of Chicago's iconic buildings
10
Lou Malnati's Pizzeria
15 minutes
Enjoy Chicago-style deep dish pizza
11
Millennium Hall
10 minutes
Enjoy a Chicago style hot dog or Italian Beef
12
Palmer House Hilton Historic Lobby
10 minutes
Visit the iconic Palmer House Hotel lobby and enjoy the original recipe brownie, invented here at the hotel for the 1893 Chicago's Worlds Fair.
13
Exchequer Restaurant & Pub
10 minutes
Enjoy an italian beef sandwich.
14
The Art Institute of Chicago
Amazing collections
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