CHICAGO SIGHTSEEING TOUR FIELD GUIDE
Holiday Hike: A Three‑Hour Taste of Chicago’s Winter Lights and Markets
A three-hour, holiday-themed walking tour by Bobby’s Bike Hike that samples deep-dish pizza, Christkindlmarket treats and the Magnificent Mile lights—this guide lays out the route, logistics and what’s included.
Holiday Hike: A Three‑Hour Taste of Chicago’s Winter Lights and Markets.
Embark on Bobby’s Holiday Hike, a three-hour walking tour that threads Chicago’s winter holiday highlights into a single afternoon stroll: warm, filling deep-dish pizza; the German-inspired Christkindlmarket; steaming hot chocolate to toast the season; and the illuminated storefronts and display lights of the Magnificent Mile. The tour runs from the end of November through Christmas Eve and is presented by Bobby’s Bike Hike.
Highlights
Outing Highlights
Magnificent Mile Holiday Illumination
The walk includes views of the Magnificent Mile’s seasonal lighting displays, offering a compact way to experience Chicago’s downtown holiday atmosphere.
Deep-Dish Pizza and Warm Treats
A warm, filling deep-dish pizza stop is built into the tour’s food sampling—part of the curated food and beverage tastings included with the ticket.
Christkindlmarket and Seasonal Sips
The route visits the German-inspired Christkindlmarket for seasonal shopping and treats, and the tour includes a hot chocolate toast; a VIP beer/cocktail upgrade is available for an additional price.
What the day feels like
What the Holiday Hike Feels Like
Over the course of three hours, you’ll move on foot between compact, seasonal stops that pair iconic Chicago sights with curated food and drink samples—an approach that compresses holiday lights, market browsing and classic Chicago fare into a single afternoon outing.
THE LIGHTS
Magnificent Mile Holiday Illumination
The walk includes views of the Magnificent Mile’s seasonal lighting displays, offering a compact way to experience Chicago’s downtown holiday atmosphere.
THE FLAVORS
Deep-Dish Pizza and Warm Treats
A warm, filling deep-dish pizza stop is built into the tour’s food sampling—part of the curated food and beverage tastings included with the ticket.
THE MARKET
Christkindlmarket and Seasonal Sips
The route visits the German-inspired Christkindlmarket for seasonal shopping and treats, and the tour includes a hot chocolate toast; a VIP beer/cocktail upgrade is available for an additional price.
Suitability
Who it's for
Who this tour suits
Practical planner
Details to review before reserving
All food and beverage samples are included in the ticket price; no separate payments are required for the included tastings.
Tickets start at $79.99; a VIP beer/cocktail upgrade is available for an additional price.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the tour?
The Holiday Hike runs for three hours.
When does the tour operate?
The holiday-themed tour begins at the end of November and runs through Christmas Eve.
Where do we meet?
The meeting point is the Plaza of the Americas at 430 N Michigan Ave, Chicago, IL 60611.
What’s included in the ticket price?
All food and beverage samples are included in the ticket price.
Are alcohol options available?
A VIP beer/cocktail upgrade is available for an additional price.
How much does the tour cost?
Prices start at $79.99.