Meet your guide in the Loop neighborhood in downtown Chicago, and then set off on your 3-hour tour to explore the city’s festive streets and top pizza joints. As you walk, chat with your guide about Chicago and its many Christmastime sights. The coldest and darkest time of the year in Chicago, the December months are also the city’s most cozy, when the shops and cafes are filled with decorations and the streets glow with sparkling holiday lights.

Stroll through Jewelers Row, the historical district that spans two blocks lined with jewelers from around the world, and on to the founding location of Chicago for some memorable winter photos. Soak up the hustle and bustle of the theater district, gaze at the famous Daley Plaza Christmas tree, and then continue to the Marshall Field Building ─ home to Macy’s ─ to see its iconic Walnut Room and tree.

While seeing the sights, enjoy stops at some of the city’s famous pizza joints to shelter from the winter cold and keep your energy topped up. Chicagoans are passionate about their pizza, and the stuffed-crust versus deep-dish pizza debate is often heard around town. Enjoy a full slice of each variation (two slices in total), and make your own mind up about your favorite authentic Chicago pizza. You can reflect on your pizza experience while sipping on hot chocolate at a famous bakery on State Street.

Before saying your goodbyes to your guide, finish with a mini canoli, Frango mint pie and a single Frango mint inside the Marshall Fields Building.