Chicago Holiday Food & Walking Tour: Festive City Highlights
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Experience the magic of downtown Chicago during the holiday season with the Chicago-Style Holiday Hike: Festive Food and Walking Tour. This 3-hour guided tour takes you through the city's most iconic seasonal attractions, offering a true taste of Chicago's festive spirit.
Sample classic Chicago favorites like deep-dish pizza, a Chicago-style hot dog, Italian beef, and sweet treats like brownies and hot apple cider. Your local guide will share lively stories—such as how Rudolph the Red-Nosed Reindeer originated in Chicago—and lead you to must-see sights like the holiday windows at Marshall Field's, Millennium Park's ice rink, and VIP access to the Christkindlmarket.
With a mix of delicious bites, stunning sights, and festive tales, this tour provides a comprehensive and memorable Chicago holiday experience. Perfect for those wanting to immerse themselves in the city's holiday traditions and vibrant atmosphere.
Frequently asked questions
How long is the tour?
The Chicago-Style Holiday Hike lasts approximately 3 hours.
What languages are available?
The tour is conducted in English.
What is the group size?
Groups are limited to up to 15 participants.
Is the tour suitable for children and accessibility needs?
Yes. The tour is wheelchair accessible, and infants (0-3 years) and small children can ride in a pram or stroller.
What is included in the tour?
You’ll enjoy iconic Chicago foods like deep-dish pizza, Italian beef, a Chicago-style hot dog, brownies, hot apple cider, and festive bites. Plus, VIP entry to Christkindlmarket and stories from a local guide.
Are drinks included?
Alcoholic beverages are not included, but you can add local drink samples for a fee during the tour.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 3 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Tender Italian beef soaked in rich jus, warming you up like the perfect savory holiday comfort.
- A Chicago dog loaded with bold flavors—bright, zesty, and perfect for a festive winter bite.
- The original brownie—rich, warm, and fudgy, a sweet holiday treat that melts into pure joy.
- Enjoy deep dish pizza, Italian beef, a Chicago-style hot dog, brownies, hot apple cider, and festive bites that make this Chicago Food Tour a Holidays and Christmas feast of iconic city flavors.
- Hot Christkindlmarket cider—steaming, spiced, and soul-warming, the perfect festive winter sip.
- Savor Chicago-style pizza, a warm Christmas and Holidays favorite baked to perfection.
- Led by a local English-speaking guide
Not included
- $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
- Hotel pickup and drop-off
- Local drink samples can be added for a fee (Three 9oz pours)
Itinerary
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Skip the lines at Christkindlmarket
Enjoy steaming mugs of spiced apple cider amidst holiday stalls, twinkling lights, and festive music, capturing the warmth of Chicago Christmas in a European winter village setting.
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Deep-dish pizza indulgence
Visit a legendary Chicago pizzeria—Lou Malnati’s, Giordano’s, or Pizzeria Uno—and savor the rich, cheesy, and hearty slices that define Chicago’s pizza scene.
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Chicago Christmas Tree at Millennium Park
See the towering, decorated Christmas tree in Millennium Park, a symbol of community and holiday magic, with a tradition of donating the tree from local families.
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Ice skating at Millennium Park
Experience the joy of skating beneath Chicago’s skyline at the free public rink, or simply enjoy the festive scene with twinkling lights and holiday music.
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Stroll along Michigan Avenue
Walk the Magnificent Mile, lit up with thousands of holiday lights, and enjoy the festive atmosphere of one of the world’s premier shopping streets.
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Wrigley Building holiday glow
Admire the historic Wrigley Building decorated for the holidays, with its illuminated façade and charming seasonal décor.
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Chocolate treat at Palmer House Hotel
Taste the original brownie from 1893 in the elegant Palmer House Hotel, surrounded by holiday décor and history.
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Visit Jay Pritzker Pavilion
See the iconic pavilion with its flowing steel design, a hub of cultural activity and holiday energy in Millennium Park.
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Italian beef sandwich
Sample Chicago’s famous Italian beef—thin slices of slow-roasted beef soaked in au jus, topped with peppers or giardiniera, a true city comfort food.
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Macy’s holiday window displays
Walk past Macy’s and enjoy the whimsical holiday windows filled with storybook scenes, lights, and festive charm.
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Cloud Gate reflections
Stand beneath the 'Bean' and marvel at the holiday reflections and sparkling cityscape in this Chicago icon.
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Art Institute lions in holiday wreaths
See the famous bronze lions adorned with wreaths, a beloved Chicago holiday tradition and perfect photo op.
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Millennium Park holiday sights
Enjoy the festive scene of the ice rink, Christmas tree, and park lights, all atop a unique rooftop landscape engineered as a 'living roof.'
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Chicago-style hot dog
Taste the classic hot dog 'dragged through the garden,' topped with mustard, relish, onions, tomato, pickle, peppers, and celery salt—an iconic holiday snack.
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Daley Bicentennial Plaza
Relax in this peaceful, snow-dusted park, designed as a quiet refuge with softly lit trees and open pathways, honoring Chicago’s bicentennial history.
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State Street holiday sparkle
Stroll along State Street, illuminated with thousands of lights and home to Chicago’s famous Thanksgiving Parade, celebrating the start of the season.
Meeting point & pickup
Meet at the starting point
Departure Point: Plaza of the Americas - Northside of Wrigley Building - Michigan Avenue ground level (next to the BIG ANGEL WINGS). Your guide will be wearing a Bobby's Bike Hike shirt with a branded paddle. The tour begins here in Chicago.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day before
- 0% refund if cancelled within 24 hours of the start
- Tour may be canceled if there are not enough travelers
Instant confirmation
Your booking is confirmed immediately after checkout.
From $84.99 per person
- Free cancellation
- Secure checkout with our booking partner
