Top Weird Tours to Take On Your Chicago Trip

The architectural tour is fascinating, and the tour of towering lakeside skyscrapers is cool and all… but where are they hiding all the good stuff? Chicago is a city that’s packed with weird history, seedy happenings, ghost stories, and oddities.

In a place that’s notorious for gangsters, bizarre tragedies, and an old history that’s built on fun legends, it’s no surprise that Chicago boasts some captivatingly weird tours for its visitors (and even lifelong residents) to learn something new and experience something out of the ordinary.

Don’t miss some of these unique tours of The Windy City:

 

The Devil in the White City Tour

Now is the perfect time to book this grisly tour of Chicago. Leonardo DiCaprio and Martin Scorsese are teaming up to produce a movie adaptation of the 2003 Erik Larson bestseller that was inspired by the real killing spree that occurred during the 1893 Chicago World’s Fair.

One of America’s most infamous serial killers, H. H. Holmes, created his gruesome “Murder Castle” in Chicago in order to turn visitors of the World’s Fair into his victims. The structure no longer stands, but this tour will take you to the site where it became the many victims’ last living location, and they’ll take you to the notable sites that once housed the World’s Fair, and give you a detailed glimpse into a dangerous and beautiful point in Chicago’s storied history.

 

The Untouchables Tour

From the safety of several decades later, the gangster-controlled city of Chicago seems like a lively story. But not long ago, every day was life or death during the battle for the soul of the city between the Feds and the mob.

Climb aboard Chicago’s old black school bus and have costumed, tommy-gun-toting gangsters show you around sites like the Biograph Theatre where John Dillinger finally met his violent end, the scene of the St. Valentine’s Day Massacre, the Holy Name Cathedral, Dion O’Banion’s flower shop, and other haunts of the most notorious gangsters in Chicago’s history.

You’ll feel like you got on a bus and went back to the 1920’s, complete with a few classic evasions from the Feds and rival gangs.

 

Chicago Pizza and Chocolate Tours

The chocolate and pizza tours are two separate (and magical) things, but we’ve combined them to peak the interest of everyone who loves two of the greatest culinary inventions of all time. The 2.5 hour chocolate tour of Chicago will take you to bakeries and sweet shops ranging from the internationally famous to the tiny, family-owned shops that hold the secrets to the sweets.

The Chicago Pizza tour is the ultimate exploration of one of Chicago’s most important contributions to the world: deep dish pizza done right. The 2.4 hour tour will take you through the neighborhoods of Chicago, sampling the best of the city’s pizza “one slice at a time.”

 

The Chicago Hauntings Signature Ghost Tour

Chicago’s “Ghost Bus” will be your guide through some of the Windy City’s most beloved “haunts.” They’ll walk you through some of the ghost stories you’ve never heard of, as well as some of the city’s most famous haunted locations, including supernatural sites like the tragic Iroquois Theatre & Death Alley, the death site of Resurrection Mary, haunted Graceland Cemetery, Hull House, the haunted places of Streeterville, and more.