What To Expect

The adventure begins at Lou Malnati’s Pizzeria in the Wrigley Building (410 N. Michigan Avenue) right on Chicago’s Magnificent Mile, which is Chicago’s largest holiday shopping district and hosts the unofficial start to the Christmas season each year with its Holiday parade down its corridor. Here you’ll meet your fun-loving and enthusiastic tour guide who will introduce you to the beautiful city and our history of holiday cheer. Your group will share a hot, cheesy, deep dish pizza, one of Chicago’s favorite holiday meals—often shipped around the country as a gift! You’ll learn about the history of this Goliath pie and taste why it’s become a global phenomenon. Guests over 21 years will be able to upgrade their ticket to the VIP Christmas cocktail/Craft beer package to enjoy a locally crafted Chicago beer with their pizza.

After pizza, your guide will lead you on an amazing journey where we’ll see the Wrigley Building and it’s beautiful Christmas tree and holiday decor, then a beautiful walk over the Chicago Riverwalk to make a stop at the Chicago Theatre and it’s iconic Chicago marquee. By this point in the tour we’ve opened your appetite back up to enjoy a traditional Chicago-style hot dog at Billy Goat Tavern, a local favorite made famous by the famous SNL skit. Their Chicago-style hot dogs are served with all the traditional fixings as well as vienna beef, the preferred beef hot dogs of Chicago.  Guests over 21 years will be able to upgrade their ticket to the VIP Christmas cocktail/Craft beer package to enjoy a locally sourced and seasoned craft beer sample or holiday cocktail.

Then we’re off to Millennium Park. Here you’ll get a full tour and catch a peek of some of our favorite (and most-heavily Instagrammed) works of public art such as Cloud Gate (aka ‘the Bean’), the Pritzker Pavilion, the Crown Fountain, and Chicago’s city Christmas Tree. You’ll learn about Chicago’s long history of Christmas tree distribution and see the annual city Christmas tree, donned with thousands of twinkling lights. Ample photo opportunities guaranteed!

The excitement of Millennium Park will work up your hunger and we’ll satisfy that craving with another Chicago staple, the Italian beef sandwich served with sweet or hot peppers and drenched with au juis.

Next, it’s on to try the Chicago brownie, invented right here in Chicago, where we’ll relax in the elegantly-decorated lobby of the Palmer House hotel. The Palmer House is the longest continually-operating hotel in North America, but is better known for its famous dessert invention: the brownie!

The tour will then head over to State Street for a glimpse of the Christmas window displays at the flagship Marshall Field’s department store (now a Macy’s). These narrative dioramas have been drawing crowds since their debut in the 1940s, and get more creative and elaborate every year.

The tour will conclude at Chicago’s legendary Christkindlmarket, a German and European-inspired open-air holiday bizarre. Dozens of vendors from around the world set up shop in Daley Plaza to sell some of the finest holiday foods and gifts available in the city. You’ll get to taste of some delicious German holiday fair and learn about other Bobby-approved holiday activities to enjoy during your stay in Chicago before being let go to discover the market and all it has to offer.

If you’d like to skip the holiday food and just enjoy the guided holiday stroll — Chicago’s Seasonal Stroll – Walking Tour. These two holiday tours are sure to get you in the Holiday spirit, so enjoy!