Chicago Pedway Tour
The Pedway is the place to be on a midwinter day downtown, but its walkways, passages and tunnels offer a great opportunity for subterranean exploration at any time of the year. Comedian Margaret Hicks conducts an entertaining 90-minute tour of this odd underground patchwork, a place that tourists and lifelong Chicagoans alike are largely unfamiliar with.
Devil in the White City Tour
The aptly-named Weird Chicago Tours offers tours of the former stomping grounds of serial killer H. H. Holmes, made (in)famous by the 2003 Erik Larson bestseller, The Devil in the White City: Murder, Magic, and Madness at the Fair That Changed America. Holmes’ “Murder Castle” no longer stands, but tour-goers visit the site where it once stood, along with murder sites and remnants of the 1893 World’s Fair locations.
Weird & Haunted Tour
Weird Chicago Tours’ standard tour is comprised of ghost stories, crime spots and gangster lore, with rare access to sites for a hands-on tour experience. Experience the all-around strangeness of Chicago’s past in one outing, with a dynamic and knowledgeable guide.
If you’ve seen an old black-painted school bus cruising around, chances are it belongs to Untouchable Tours. The two-hour trip back to the Roaring Twenties includes stops at the Biograph Theatre, the scene of the St. Valentine’s Day massacre, Dion O’Bannion’s flower shop, Holy Name Cathedral, and other significant locations of gangster history.
The Chicago Hauntings Signature Ghost Tour
Tap into your inner ghost hunter and hop on the “Ghost Bus” for a 2.5 hour tour of storied haunting sites throughout the city. Guests are invited to investigate locations such as the Iroquois Theater & Death Alley, haunted Streeterville, the death site of Resurrection Mary, Jull House, Graceland Cemetery, and many others.
Chicago Chocolate Tour
For those who prefer a strictly culinary exploration, consider a Willy Wonka-style taste of some of the city’s traditional and non-traditional sources of chocolate goodness. The 2.5 hour Chicago Chocolate Tour visits chocolate shops, bakeries and cafes, and offers insight into the history of chocolate, with plenty of sampling. Both public and private tours are available.
Chicago Pizza Tours
For those who prefer savory over sweet, there’s the Chicago Pizza Tour. Beginning at Pizano’s in the Loop, the bus tour shows guests Chicago “one slice at a time,” covering a variety of pizza styles with stops in Little Italy, West Town, Hyde Park, Roscoe Village, and ending at Gino’s East. The tour lasts 2.5 hours and explores the history of Chicago pizzerias and pizza culture, with a generous helping of art & architecture on top.
For an alternative to the everyday ground-level tour, there Chicago Aerial Tours’ Night Flight, a scenic spin in an airplane cruising 3000 feet above the city. The city lights shine and stellar views abound as the pilot takes guests from Midway Airport west toward the lakeshore.
Explore exotic Chinatown with this lecture/lunch/walking tour package featuring local ghost stories, magical customs, and “The Ancient Practice of Geomancy” (feng shui). The tour begins at Triple Crown Restaurant, continues through shops where guests may purchase rare teas, ba-gua mirrors, foo dogs, and all manner of mini Buddha figurines before stopping at various Chinatown landmarks, including a haunted funeral home and the on Long Building. Ghost hunter Richard T. Crowe conducts.
O’Leary’s Fire Truck Tours
Billed as “the hottest tour in town,” O’Leary’s conducts tours with a fleet of modified antique fire trucks. The tour itself is a rather standard scenic overview of Chicago history and culture, but the unique tour guides and vehicles make it particularly ideal for kids, fire engine enthusiasts and anyone looking for a different kind of group outing.
Greg Wahl is a Chicagoan, a freelancer, a grad student, and a seeker of all things awesome & interesting throughout the city and beyond.