The 12 Best Crime Tours in Chicago
Chicago is one of the best cities in the US for people who love dark history. But at the same time, Chicago is known for its music scene, stunning Art Deco architecture, delicious deep-dish pizza, and the Bean!
However, Chicago is also known for its dark past during Prohibition and is tied to some of the most infamous mobsters and gangsters, including Al Capone and John Dillinger.
Head out on the town and take a go on a Chicago Mob Tour to learn all the seedy details about Chicago’s Prohibition era. Then, visit some of Chicago’s most iconic areas that Chicago’s gangsters frequented during the roaring ‘20s by taking one of the best crime tours in Chicago.
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The 12 Best Crime Tours in Chicago
1. Chicago Crime and Mob Bus Tour
The Chicago Crime and Mob Tour takes you around areas frequented by Chicago mobsters like Al Capone, The Untouchables, Hymie Weiss, and John Dillinger.
The Chicago mob tour visits the Holy Name Cathedral, Biography Theatre, and the site where the Bloody St. Valentine’s Day Massacre occurred. If you are interested in Chicago’s mob history, this is the tour for you, as you will hear thrilling stories about gangsters, violence, and crime as you are taken around the city.
This tour is one of Chicago’s best Mafia and Prohibition tours, as it visits Frank Nitti’s vault hideout. In addition, you will visit a mob museum and historic bootlegging tunnels, where you will see safes used by mobsters in the 1920s.
The tour offers an air-conditioned bus jam-packed with gangster lore. It is perfect for those seeking comfort over walking to soak up Chicago’s criminal past.
Book here: Chicago Crime and Mob Bus Tour
2. Chicago: Gangsters and Ghosts Guided Walking Tour
The Chicago: Gangsters and Ghosts Guided Walking Tour is a history-based gangster tour perfect for people who love all things spooky! The tour is all about ghosts, gangsters, and their perspectives on Chicago.
It is by far one of the best crime tours in Chicago, as it covers the South Loop, which mixes Al Capone-era gangster chat with terrifying paranormal tales from Death Valley, the Palmer House, and the extremely haunted Congress Hotel in the span of 2 hours.
Not only will you hear tales of Chicago’s dark history at each stop from a historian guide, but you will discover how Al Capone ran his empire and learn about the crazy happenings at his headquarters.
This is a family-friendly tour, and the tour guides are fun and enthusiastic, ensuring it’s exciting and unforgettable! It is the perfect mashup of mobsters and spooky spectres.
Book here: Chicago: Gangsters and Ghosts Guided Walking Tour
3. Chicago Architecture and True Crime History Tour
Learn about the skeletons behind Chicago’s gorgeous architecture on the Chicago Architecture and True Crime History Tour. Follow a local guide through downtown landmarks like Chase Tower and the Palmer House, where you will learn about the history of these stunning buildings and the dark crimes tied to each.
The guides are incredible at juggling the grisly history with architectural knowledge. It’s both enlightening and disturbing! This is an architecture-forward tour, so it’s not completely about mob lore. So if you prefer a more true crime tour, this one isn’t for you.
But it is a great tour for anyone chasing the best crime tours in Chicago, with a side of stunning skyline views.
Book here: Chicago Architecture and True Crime History Tour
4. Chicago Night Crimes Tour By Bus
Explore the dark side of the Windy City by taking the Chicago Night Crimes Tour by Bus. The Chicago mob tour explores the lives of monsters and gangsters such as Frank Nitti, Bugs Moran and Al Capone after sundown.
Hop aboard the bus as it cruises past the site of the St. Valentine’s Day Massacre and visits pubs like the Burwood Tap and Harry Caray’s Italian Steakhouse. The Chicago Night Crimes Bus Tour passes by places like Water Tower Place, North Avenue Beach, Lincoln Park, Biograph Theatre, Oz Park, Marina City, and Holy Name Cathedral. You will visit some of the sites where the most infamous criminal acts took place back during Prohibition.
What makes this one of the Best Gangster Tours in Chicago? You get to relax on a warm bus heading to the following location, which is perfect on those cold Chicago nights.
Book here: Chicago Night Crimes Tour by Bus
5. Chicago Crime, Mobsters & Ghosts Walking Tour
Are you looking for the best crime tours in Chicago? The Chicago Crime, Mobsters & Ghosts Walking Tour takes you on a night of gritty true crime and ghost stories. The tour is led by guides who lead small groups through downtown streets and alleys, including the “Alley of Death,” while sharing tales of 1920s gangsters and mysteries.
The tour runs between 90 minutes and two hours and starts near the Congress Plaza Hotel, ending on North Michigan Avenue. End the night with a nightcap after filling your evening with one of Chicago’s most memorable crime tours. It leans more toward history than toward visiting mob hideouts, so history nerds will enjoy it most.
Book here: The Chicago Crime, Mobsters & Ghosts Walking Tour
6. Haunted Chicago: Crime, Ghosts, and Capone Walking Tour
Grab your fedora and head to the old stomping grounds of renowned gangsters like Al Capone and John Dillinger on the Haunted Chicago: Crime, Ghosts and Capone Walking Tour. The tour visits former Prohibition-era speakeasies and real mob shootout sites and sneaks in ghost stories for added spookiness.
The tour is easily one of the best crime tours in Chicago as it is compact, walkable and packed with gangster charm, perfect for history fans and thrill-seekers. It also offers special access to some historic locations along the way.
Book here: Haunted Chicago: Crime, Ghosts, and Capone Walking Tour
7. Chicago: Prohibition Speakeasies Bus Tour or Walking Tour
If you are thirsty for history and want to sip drinks like a gangster, I recommend the Chicago: Prohibition Speakeasies Bus or Walking Tour. The tour takes you speakeasy-hopping through Chicago’s Roaring ’20s, visiting gangster hideouts and glitzy hotspots where high society drank alcohol in secret.
The tour is either a downtown walking tour or a neighborhood bus crawl that goes through the Gold Coast, Lincoln Park and Wicker Park. The guides on this tour are fantastic and hilarious, with deep knowledge and a knack for making Chicago’s history feel like a fun night out.
This is a drinking tour, so it is only for those over 21. Bring cash for drinks and your ID to prove you are old enough to drink them.
Book here: Chicago: Prohibition Speakeasies Bus or Walking Tour
8. Chicago’s Original Gangster Tour by Bus
Are you looking for Chicago’s most notorious mob tour experience? Hop aboard Chicago’s Original Gangster Tour by Bus and travel back in time on the Original Gangster Tour. The tour is full of costumed guides in full gangster get-up who narrate 1920s mob history by visiting the hangouts of mobsters like Moran, Dillinger and Capone.
You will hear all about the details of their haunts at sites like the Biograph Theater, Holy Name Cathedral, and the St. Valentine’s Day Massacre. The tour takes you to about 10 locations connected to Chicago’s most infamous gangsters.
This tour is loads of fun and definitely one of the best Crime tours in Chicago because you will hear lots of history and comedy from a costumed guide.
If you are looking for a small group-sized Chicago gangster tour, this is the crime tour for you, with a max of 8 travellers!
Book here: Chicago’s Original Gangster Tour by Bus
9. Chicago: Historic Gangsters & Twilight Tales Night Cruise
Why walk the crime scene when you can float past it? The Chicago: Historic Gangsters & Twilight Tales Night Cruise glides down the Chicago River past historic landmarks such as the Tribune Tower, the Wrigley Building, and the Willis Tower.
The skyline is all lit up against a twinkling night sky, making it the perfect way to spend an evening if you want to grab a cocktail while listening to horrifying tales of the Eastland disaster, the Great Chicago Fire, and serial killer H. H. Holmes.
If you’re after one of the best crime tours in Chicago and want to sail the high seas (okay, the river), this evening cruise delivers dark history, dazzling architecture, and just enough spookiness to send shivers down your spine.
Book here: Chicago: Historic Gangsters & Twilight Tales Night Cruise
10. Chicago Gangsters and Ghosts Walking Tour
If you want to go on a crime tour in Chicago with a paranormal twist, I recommend the Chicago Gangsters and Ghosts Walking Tour. The two-hour downtown walking tour is heavier on ghosts than on gangster history, so go in expecting more supernatural tales than speakeasy spirits.
Stops include the historic Palmer House Hilton, Cloud Gate, and the Chicago Theatre, and it ends at the iconic Congress Plaza Hotel. It’s a fun tour that lets you explore Chicago’s dark side, but the ghosts steal the show from the gangsters.
Book here: Chicago Gangsters and Ghosts Walking Tour
11. Chicago’s Dark Side: Ghosts, Gangsters, and True Crime Tour
If you’re hunting for the best crime tours in Chicago that offer gritty history, gangster hideouts, tales of restless spirits, and the history of the disasters that shaped the city, I recommend Chicago’s Dark Side: Ghosts, Gangsters, and True Crime Tour.
The small-group walking tour strolls through River North and downtown, offering insider access to haunted hotels and making it the perfect spooky crime tour. The tour guides are passionate and really know their history. The tour wraps up at the haunted Congress Plaza Hotel, which offers the perfect eerie finale to Chicago’s true crime history.
Book here: Chicago’s Dark Side: Ghosts, Gangsters, and True Crime Tour
12. The Devil in the White City: A Haunting History Tour
Do you want to go on more Crime tours in Chicago but hear about more than just Al Capone? The Devil in the White City explores the history surrounding the legend of the notorious H.H. Holmes.
The tour takes you around Chicago by bus for three hours of the insanity surrounding the 1893 Chicago World’s Fair. In addition, you will visit sites hit by H.H. Holmes, including Jackson Park, Midway Plaisance Park and the elusive Murder Castle of H.H. Holmes!
If you love Chicago crime tours and have done the rest, I highly recommend this tour.
Book here: The Devil in the White City: A Haunting History Tour