The 9 best crime tours of Chicago

Follow in the footsteps of infamous gangsters like charming bank robber John Dillinger and Polish mobster Hymie Weiss on this bus tour. You’ll hear stories about the who’s who of Chicago organized crime, drive by a few murder locations and spot the historic courthouse where many criminals were thrown in the clink. 

Time Out tip: Brush up on your crime knowledge for the post-tour quiz. 

The towering skyscrapers and shining facade of Cloud Gate might make the Loop seem glitzy and glamorous, but it was once a hotspot for vice. In the ’20s and ’30s, this nabe was the epicenter of bootlegging and gangbanging in Chicago. Take a walking tour through the area to spy speakeasies, secret underground tunnels and maybe even a ghost or two.

Time Out tip: The meeting point is just outside the Wyndham Hotel – take that as our accommodation suggestion. 

There are endless upsides to taking tours of a city, but there are downsides as well—most notably, not being able to explore at your own pace. That’s not the case with the self-guided Vice, Crime and Gangsters in Chicago tour. The 31-stop audio tour starts at the Dusable Bridge and winds its way through notorious locations in the Loop and River North, including Chicago’s first vice district and the site of the Lager Beer Riot. It’s narrated by professor, urban historian and former journalist Richard Junger.

Time Out tip: If you want to get familiar with your guide before the tour, have a skim-read of the books he's written on Chicago history. 

See the sites of grisly killings under the dark of night on this evening bus tour. You’ll visit the Biograph Theater where Dillinger met his end, the site of the St. Valentine’s Day Massacre and other infamous locations. The bus even stops at a few historic watering holes like Harry Caray's so you can raise a glass to the city's dearly departed criminals.

Time Out tip: Don't worry about trying to snap pics from the window of the bus – photo stops will be granted. 

On the surface, ghost tours and crime tours are two separate entities. But how does one become a ghost? Death. And how does someone’s death become notable enough to end up on a tour? It’s got to have some sort of criminal element, right? This ghost investigation tour is led by a paranormal investigator who takes guests through some of the eeriest locales in Lincoln Park, including the site of the St. Valentine’s Day Massacre. It also offers an opportunity to use paranormal activity-detecting equipment to help you determine if you just saw a ghost or a very exhausted DePaul student.

Time Out tip: Keep your eyes peeled for the Victorian woman in white at Lincoln Park Zoo. 

This notorious gangster's trademark look – thick eyebrows, jaunty hat, heavy overcoat and a cigar hanging from his lips – became the basis of the stereotype of the mafia man. he got his start in New York as a member of the Five Points Gang before founding the Chicago Outfit and wreaking havoc on the Midwestern city. Follow this Al Capone tour of Chicago in a private town car – in true mafioso style.

Time Out tip: Get a team of five together to get the best value group ticket. 

In addition to a thriving mob community, Chicago was also home to one of the country’s first known serial killers: H. H. Holmes. The insurance scammer and con man lured hundreds of people to the three-story hotel that would later be known as the Murder Castle: a labyrinth of trap doors, peepholes, dead-end stairways, gas chambers and crematorium that he used to murder his victims and dispose of their remains. To this day, authorities still don’t know how many people he might have killed. Learn the disturbing facts of the case on a Weird Chicago walking and bus tour.

Time Out tip: There's a restroom on board – always a win. 

After a long night of making dirty deals and plotting the downfall of their enemies, Chicago mobsters used to unwind with some booze and live music at a mafia-friendly bar. You’ll do the same on this private guided tour that hits several historic landmarks before stopping for a drink at a bar formerly owned by Capone himself.

Time Out tip: Plan this tour around a big night out, as it's a great way to get the party started before hitting the town when everyone's parted ways. 

For more than 30 years, Untouchable Tours has been driving tourists back and forth across the city to see Chicago's more unconventional sights, including the staircase in front of a church that’s covering up bullet holes, and the empty lot where the St. Valentine’s Day Massacre took place. The two-hour tour features guides that take on the persona (and snappy garb) of ’20s gangsters. Guides tell the tales of prohibition-era Chicago and what it was like when gangsters like Al Capone, Bugs Moran and Hymie Weiss walked the streets.

Time Out tip: One to book in advance for.