Holiday Hike Chicago-Style: Festive Food & Walking tour in Chicago booking from $84.99

Holiday Hike Chicago-Style: Festive Food & Walking tour

Overview

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!

City: Chicago

Mon 02 Jun

Other dates

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Starting at $84.99

Make a reservation

Mon 02 Jun

Starting at $84.99

Make a reservation

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What's Included

Food samples

Holiday attractions

Holiday Cocoa or Cider

Local tour guide

Additional Info

Wheelchair accessible
Public transportation options are available nearby
Suitable for all physical fitness levels
If you have dietary restrictions, please add a note in the special requirements section when booking, and email to [email protected] after booking to confirm they can accommodate.
Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets.
VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+)
TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002.
Our groups have exclusive VIP access to locations we visit.
Operates in all weather conditions, please dress appropriately
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.

What To Expect

Christkindlemarket

Enjoy a hot cider at this outdoor german christmas market

Palmer House Hilton Historic Lobby

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.

Macy's on State Street

Enjoy the Holiday decor

Millennium Park

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.

Cloud Gate

Iconic Chicago attraction

Jay Pritzker Pavilion

Gorgeous open air amphitheater

Daley Bicentennial Plaza

Enjoy Christkindlmarkt in Chicago

Wrigley Building

Visit one of Chicago's iconic buildings

Palmer House Hilton Historic Lobby

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.

The Art Institute of Chicago

Amazing collections

Show 7 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (64)

Kasey_E

Dec 2024

I had an amazing time on this tour! Jamal was my tour guide. He was so nice and had great information about the restaurants and the city. I tried a lot of food I wouldn't have gotten on my own, and was able to see a lot of the city in only 3 hours. My only suggestion would be for the tour to arrange our apple cider in a souvenir mug!

Steve_G

Dec 2024

We had Mickey as our guide and he was absolutely amazing!!! Super informative, friendly and funny! He did an amazing job and took us to some really cool spots.

Wendy_W

Dec 2024

Hi, I had Lilian for our group leader. I know I didn’t spell her name right but she was wonderful. I loved hearing about the history and everything of Chicago. I have been to Chicago in 2008 but had not taken this tour before obviously cause this was a holiday hike got to see like Christmas stuff and everything. The only thing I wish is that I thought we were gonna go inside the Palmer house so I’m gonna make an effort to go by today. I haven’t tried my brownie yet, but I wanna go in there and just look around because of the history other than that everything else was wonderful on the trip

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Holiday Hike Chicago-Style: Festive Food & Walking tour

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