Chicago: Guided Holiday Walking Tour and Food Sampling

Chicago’s guided holiday walking tour offers a compelling blend of sightseeing and culinary delights. Visitors can expect to marvel at the city’s iconic landmarks, sample its renowned local cuisine, and enjoy the festive spirit of the season. From the dazzling Millennium Park to the historic Palmer House Hotel, this 3-hour experience promises a well-rounded exploration of the Loop area. With an optional VIP package featuring adult beverage sampling, the tour caters to a range of interests and preferences. Whether you’re a first-time visitor or a seasoned Chicagoan, this guided adventure promises to unveil the city’s enchanting holiday charm in a way that may just surprise you.

This experience made our list of the 20 Best Food Tours In Chicago.

Key Points

• This guided walking tour showcases the festive sights and iconic culinary offerings of Chicago’s Loop area during the holiday season.
• Highlights include exploring Millennium Park’s Christmas tree and ice-skating rink, sampling the original brownie, and indulging in Chicago-style pizza and hot dogs.
• The 3-hour tour provides an opportunity to warm up with a cup of hot apple cider and upgrade to a VIP package for adult beverage sampling.
• The tour meeting point is conveniently located near Millennium Park, with easy access to public transportation and nearby parking.
• Comfortable, weather-appropriate attire and walking shoes are recommended for this tour that runs rain or shine.

You can check availability for your dates here:

Overview of the Tour

This guided holiday walking tour takes participants through Chicago’s iconic Loop area, showcasing the city’s magic and tradition during the festive season.

Over the course of 3 hours, the tour explores Millennium Park’s dazzling Christmas tree and ice-skating rink. Guests can warm up with a cup of hot apple cider as they discover the city’s famous culinary offerings, including the original brownie at the historic Palmer House Hotel and iconic Chicago-style pizza and hot dogs.

An optional VIP package allows participants to sample adult beverages. With a knowledgeable guide, comfortable attire, and a willingness to explore, this tour provides a delightful holiday experience in the heart of Chicago.

Highlights of the Experience

Millennium Park’s dazzling Christmas tree and ice-skating rink beckon visitors to experience the city’s festive charm.

Guests can warm up with a refreshing cup of hot apple cider as they explore Chicago’s renowned culinary scene, savoring the original brownie at the historic Palmer House Hotel and indulging in iconic Chicago-style pizza and hot dogs.

For those seeking a more indulgent experience, an optional VIP package offers adult beverage sampling.

The tour highlights include:

• Exploring Millennium Park’s Christmas tree and ice-skating rink
• Sampling the original brownie at Palmer House Hotel
• Tasting Chicago’s famous pizza and hot dogs

Included in the Tour

The guided tour includes a feast of Chicago’s signature food items, such as the original brownie from the historic Palmer House Hotel and the city’s renowned deep-dish pizza and hot dogs. Visitors can also warm up with a refreshing cup of hot apple cider as they explore the holiday sights. Plus, an optional VIP package offers adult beverage sampling for those seeking a more indulgent experience.

Included in the Tour	VIP Upgrade
Food and non-alcoholic drinks	Adult beverage sampling
Guided tour	–
–	$19.99 per person

Meeting Point and Location

The tour meets at Lou Malnati’s Pizzeria, located at 410 N. Michigan Avenue in downtown Chicago’s bustling Loop district.

This well-known pizza restaurant serves as the convenient starting point for the guided holiday walking tour. From there, the group will embark on a 3-hour exploration of Chicago’s stunning winter wonderland.

Lou Malnati’s is situated just steps away from Millennium Park, the iconic destination for the tour.

The pizzeria is easily accessible by public transportation, with nearby stations for the ‘L’ train and numerous bus lines.

Ample parking options are available in the surrounding area for those driving to the tour.

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Recommended Attire and Weather

When attending this guided holiday walking tour, visitors are encouraged to dress in comfortable clothing and shoes suitable for the Chicago winter weather. Layering is advised, as the tour will involve both indoor and outdoor activities during the 3-hour experience.

The tour runs rain or shine, so guests should be prepared for potential rain or snow. Warm coats, gloves, and hats are recommended to stay comfortable while exploring the Loop area and Millennium Park.

Comfortable walking shoes are a must, as the tour involves several miles of walking. By dressing appropriately, guests can enjoy the highlights of the tour without being distracted by the cold or wet conditions.

Tour Schedule and Timing

Typically, the guided holiday walking tour through Chicago’s Loop area lasts approximately 3 hours, offering visitors a comprehensive exploration of the city’s festive sights and flavors.

The tour schedule is designed to allow participants ample time to enjoy the holiday atmosphere, with highlights such as:

• Visiting Millennium Park to admire the towering Christmas tree and ice-skating rink
• Warming up with a cup of hot apple cider
• Indulging in the original brownie at the historic Palmer House Hotel and sampling classic Chicago-style pizza and hot dogs

The tour runs rain or shine, ensuring that visitors can experience the magic of Chicago’s holiday traditions regardless of the weather conditions.

VIP Drink Package Upgrade

For an additional $19.99 per person, the tour’s VIP Christmas adult beverage sampling package offers visitors the opportunity to enhance their holiday experience with a selection of festive alcoholic drinks.

This optional upgrade allows participants to warm up with a delightful array of seasonal cocktails, from mulled wine to spiked hot apple cider.

The VIP package provides a chance to indulge in the celebratory spirit of the season, complementing the tour’s culinary highlights.

Whether seeking to try unique holiday-themed libations or simply to add an extra touch of merriment to their exploration of Chicago’s festive traditions, the VIP drink package is an enticing option for those looking to make the most of their guided holiday walking tour.

Gratuity for the Guide

A 15-20% gratuity for the guide is suggested, as is customary for such guided tours to acknowledge the expertise and effort provided in delivering an informative and enjoyable experience.

Tipping the guide is a considerate way to show appreciation for their hard work in:

• Sharing fascinating historical and cultural insights about the sights along the tour
• Efficiently navigating the group through the busy city streets and coordinating logistics
• Ensuring everyone has a memorable and pleasant holiday adventure in Chicago

While the gratuity amount is discretionary, providing a tip that falls within the suggested range is a thoughtful gesture that helps make the guide’s efforts worthwhile.

Recap

The Chicago guided holiday walking tour offers a delightful way to experience the city’s festive charm and iconic sights.

Visitors can enjoy the holiday spirit, sample local cuisine, and even upgrade to a VIP package with adult beverage sampling.

Whether you’re a local or a visitor, this tour provides a perfect blend of sightseeing and culinary exploration in the heart of Chicago.

You can check availability for your dates here: