Chicago-Style Holiday Hike: Festive Food & Walking Tour for a Delicious Seasonal Adventure

Mon, Dec 01, 2025 07:00 AM - Wed, Dec 31, 2025 15:00 PM

Chicago-Style Holiday Hike: Festive Food & Walking Tour for a Delicious Seasonal Adventure

Mon, Dec 01, 2025 07:00 AM - Wed, Dec 31, 2025 15:00 PM

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Overview

There’s nothing quite as magical as downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3-hour guided walking and food tour through the Chicago Loop, offered by Bobby's Bike Hike, a company internationally renowned for their exceptional tours. Along the way, you’ll savor the Windy City’s favorite winter treats, including a slice of deep-dish pizza, a classic Chicago-style hot dog, Italian beef, a rich chocolate brownie, and warm hot apple cider. Upon arrival, you have the option to upgrade with a VIP holiday craft beer package for just $19.99 per person. Our lively and knowledgeable guides will ignite your holiday spirit with delicious food and fascinating stories—did you know Rudolph the Red-Nosed Reindeer was created right here in Chicago? You’ll also enjoy iconic sights like 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 a complete and festive Chicago holiday experience!

About this Event

Departure Point
The tour begins at Lou Malnati's Pizzeria at the Wrigley Building. Please note, the entrance is on the north side of the Wrigley Building at ground level. Your guide will be easy to spot, wearing a Bobby's Bike Hike shirt and holding a paddle.

Duration
Approximately 3 hours

Languages Available
Tours are led in English by a live guide.

Points of Interest and Stops

Christkindlmarket (50 W Washington St): Savor hot cider at Chicago’s beloved outdoor German Christmas market (10 minutes).
Palmer House Hilton Historic Lobby (17 E Monroe St): Walk along State Street to see dazzling lights and window displays, then sample the original brownie inside this historic hotel as your guide highlights its grand architecture (15 minutes).
Macy’s on State Street (111 N State St): Take in the festive holiday decor (10 minutes).
Millennium Park: Get a full tour of the park, view the outdoor ice-skating rink, and see Chicago’s official Christmas tree (1 hour).
Cloud Gate (201 E. Randolph St.): Visit the iconic “Bean” sculpture (5 minutes).
Jay Pritzker Pavilion: Admire this beautiful open-air amphitheater (5 minutes).
Daley Bicentennial Plaza (337 E Randolph Dr): Enjoy more of Christkindlmarket’s festive atmosphere (20 minutes).
Chicago Christmas Tree: Stop by the city’s official Christmas tree (5 minutes).
Wrigley Building (400-410 Michigan Ave): Visit this Chicago landmark (5 minutes).
Lou Malnati’s Pizzeria (410 North Michigan Avenue): Enjoy a slice of classic Chicago deep-dish pizza (15 minutes).
Millennium Hall (11 North Michigan Avenue): Sample a Chicago-style hot dog or Italian beef (10 minutes).
Palmer House Hilton Historic Lobby (second visit): Taste the original brownie, invented for the 1893 World’s Fair (10 minutes).
Exchequer Restaurant & Pub (226 South Wabash Avenue): Try an Italian beef sandwich (10 minutes).
The Art Institute of Chicago: View the exterior of this world-class museum (duration not specified).

Additional Information

Wheelchair accessible and close to public transportation.
Suitable for all fitness levels.
Dietary restrictions can be accommodated for vegetarians and those who avoid beef or pork, but gluten-free and vegan options are very limited. Please notify the operator in advance.
VIP Adult Beverage upgrade (three craft beer samples) available for $19.99 per person (ages 21+).
The tour operates in all weather, so dress appropriately.
Minimum group size applies; if not met, you’ll be offered an alternative date or a full refund.
The tour has received TripAdvisor’s highest-level Traveler’s Choice Award every year since 2002.
Groups enjoy exclusive VIP access at each stop.

Inclusions

Food tastings
Visits to holiday attractions
Holiday cocoa or cider
Local guide

Exclusions

Suggested guide gratuity of $10 per person (cash, Venmo, or PayPal)
Hotel pickup and drop-off

Redemption Instructions

Arrive 15 minutes before your scheduled tour time.
Wear comfortable, weather-appropriate clothing and shoes.
Bring a bottle of water and use the restroom before arrival.
Tours run rain or shine.
For dietary restrictions, email reservations@bobbysbikehike.com after booking.

Voucher Info

Both mobile and paper tickets are accepted.
This tour is offered through Viator; Groupon is not affiliated with Bobby’s Bike Hike for this deal. For questions about the offer, contact Groupon customer service.

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