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 the 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 one 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.
The 11 Best Crime Tours in Chicago
Gangsters and Ghosts Tour in Chicago
Step back in time by following a historian tour guide on the Gangsters and Ghosts Tour in Chicago. The tour takes you back to the 1920s when the Chicago Loop was the hangout of the infamous gangster Al Capone.
During the prohibition, The Loop was the breeding ground for criminal activities, including illegal speakeasy saloons, secret underground tunnels, bootleggers and the headquarters for gangsters.
The Chicago gangster tour will take you to sites that gangsters frequented, including the Congress Hotel, Millennium Park, Death Alley, and the Palmer House, Chicago’s oldest hotel rumoured to be haunted.
The tour is one of the best Crime tours in Chicago, as it has a great mix of Gangsters and ghosts, so it is perfect for people who love both. I took the tour with tour guide Alan, and he was incredibly engaging and enthusiastic.
This tour is perfect for locals and visitors to Chicago. You will leave learning something new! I highly recommend taking this tour if you want to learn more about Chicago’s dark history and all about Chicago’s prohibition era.
Book here: Gangsters and Ghosts Tour in Chicago
Chicago Crime and Mob Bus Tour
The Chicago Crime and Mob Tour carts 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 Chicago.
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.
Book here: Chicago Crime and Mob Bus Tour
Chicago: Gangsters and Ghosts 2-Hour Walking Tour
The Chicago: Gangsters and Ghosts 2-Hour Walking tour is a history-based Chicago gangster tour that is perfect for people who love all things spooky! The tour is all about ghosts, gangsters and their perspective of Chicago.
This tour takes you through the Chicago Riverwalk, The Chicago Theatre, Palmer House, Cloud Gate, the Art Institute of Chicago and the Congress Plaza Hotel & Convention Center. You will hear tales of Chicago’s dark history at each stop from a historian guide.
You will find out how Al Capone ran his empire and learn about all of the crazy happenings that occurred at Al Capone’s headquarters. In addition, you will visit all of the haunted places in Chicago and hear about the ghosts that still haunt each site.
This is a family-friendly tour, and the tour guides are fun, enthusiastic and ensure the tour is exciting and unforgettable!
Book here: Chicago: Gangsters and Ghosts 2-Hour Walking Tour
Chicago Night Crimes Bus Tour
Explore the dark side of the windy city by taking the Chicago Night Crimes Bus Tour. The Chicago mob tour explores the lives of monsters and gangsters such as Frank Nitti, Bugs Moran and Al Capone. The tour has a great pace as you are taken around Chicago’s gangster-related locations.
The tour visits local 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 the 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 Bus Tour
Untouchable Tours Chicago’s Original Gangster Tour
Take a minibus back in time on the Orginal Gangster Tour to Chicago in the 1920s 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 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.
The Untouchable Tours Chicago’s Original Gangster Tour is excellent for older kids and adults. The guides are absolutely fantastic and super engaging.
If you are looking for a small group sized Chicago gangster tour, this is the crime tour for you as they have a max of 8 travellers!
Book here: Untouchable Tours Chicago’s Original Gangster Tour
1920s Chicago Walking Tour: Art Deco, Flappers, Gangsters, and Prohibition
Step back to the roaring 20s on the 1920s Chicago Walking Tour and see some of Chicago’s gorgeous hidden gems. You will explore all of the Art Deco architecture that lines the city now and shows you how glitzy and glamorous Chicago was during the prohibition.
The walking tour explores the exteriors and interiors of buildings that were once the hotspots for flappers, jazz musicians, speakeasies and the notorious gangsters who would spend time in each location.
You will also visit an old gangster headquarters where you will see photos, newspaper clippings and a vault that Al Capone and other gangsters used. You will also visit “The Loop,” which is in downtown Chicago and the site of Chicago’s spectacular art deco buildings.
Book here: 1920s Chicago Walking Tour: Art Deco, Flappers, Gangsters, and Prohibition
Vice, Crime and Gangsters in Chicago: A Self-Guided Audio Tour
Do you want to go on all of the Crime tours in Chicago but don’t want to spend time with other people? Same. You can do that by taking the Vice, Crime and Gangsters in Chicago Self-Guided Audio Tour!
The self-guided tour takes you to sites like the DuSable Bridge, Chicago River, Franklin-Orleans Street Bridge, Chicago Riverwalk, and Wrigley Building.
In addition, you can take your time exploring Chicago’s local haunts of the prohibition era’s infamous gangsters. If you want to do the whole tour in real-time, it will take at least 75 minutes.
The audio tour provides you with tales of Chicago’s dark history and the opium trade with the sweet sounds of urban historian Richard Junger’s voice.
Book here: Vice, Crime and Gangsters in Chicago: A Self-Guided Audio Tour
Lincoln Park Hauntings Ghost Investigation Tour
Do you love ghost tours but want to dig a little bit deeper? Spend the evening with a paranormal investigator looking for all the ghosts haunting Chicago’s dark streets on the Lincoln Park Hauntings Ghost Investigation Tour.
You will visit the old City Cemetery, Couch Tomb and Lincoln Park, where you will hear about the history of the Great Fire of 1871 and more.
This is the perfect tour for people who want to go on one of the Crime tours in Chicago but want a paranormal twist. Plus, you will get the chance to use paranormal equipment and try to contact the spirits yourself!
Tour guide Tony is phenomenal and will go into great detail about all things Chicago during the prohibition and beyond.
Book here: Lincoln Park Hauntings Ghost Investigation Tour
Sin and Suds Chicago Beer Tour
Do you want to spend a few hours exploring Chicago on a gangster-themed beer tour? Then, head out on the town with the Sins and Suds Chicago Beer Tour.
You will visit Chicago’s Loop and South Loop neighbourhoods sipping on the best beer and pizza Chicago offers while hearing the tales of the mafia scene of the 1920s.
You will visit up to four local bars, and samples of beer and pizza are included in the tour price. If you want a bit more to drink, be sure to bring some cash with you.
Book here: Sin and Suds Chicago Beer Tour
The Devil in the White City: A Haunting History Tour
Do you want to go on more Crime tours in Chicago but want to hear about more than Al Capone? The Devil in the White City explores the history surrounding the legend of the notorious H.H. Holmes.
The tour carts you around Chicago by bus for three hours of the insanity surrounding the 1893 Chicago World 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