Ask an out-of-towner what they want to do when they visit Chicago, and they'll probably tell you they want to chow down on some deep-dish pizza. Chicago Pizza Tours owner and pizza aficionado Jonathan Porter leads parties on treks to some of the Windy City's most celebrated pizzerias with three different pie-themed tours. Guests sample Chicago's signature style with the deep-dish only holiday walking tour, enjoy slices with sides of adult beverages during pizza and cocktails outings, or visit the kitchens of four different restaurants during the original tour. Each outing takes visitors to local favorites across a wide range of styles and cuisines, from the caramelized thick crusts of Pequod's, the stuffed pies of Bacino's, or the Neapolitan-style creations of Spacca Napoli.

Recently, Jonathan Porter has teamed up with local writer and tour guide Jonathan Knotek to launch Chicago Prohibition Tours, a romp through some of Chicago's most famous speakeasies still in existence. During the 3.5-hour bus trip through the roaring '20s and beyond, guests can visit the old one-time haunts of gangsters and crooked pols, such as the Green Door Tavern or the Exchequer Restaurant and Pub, all while sipping popular cocktails from almost 100 years ago and communicating only through silent-film title cards.