Chicago's most-reviewed gangster and ghost walk on GetYourGuide mixes Al Capone's South Loop with the city's ghost stories, and it ends at the Congress Plaza Hotel. Below: that walk, the bus tour that covers the Lincoln Park crime scenes, a food walk, a speakeasy crawl and a night cruise, compared on price, length and who each one suits.
Updated · Prices and ratings read from GetYourGuide on 21 October 2026 · All walking tours
2 hourstop-rated walk
$31from, per person
4.7★1,880 GetYourGuide reviews
1.5 mileswith a 20-minute break
24 hoursfree cancellation window
01 · The Short Answer
Book the Gangsters and Ghosts Walk, Unless You Want Lincoln Park
The Chicago: Gangsters and Ghosts Guided Walking Tour by Empire Tours & Productions is the one most people should book. It has the most reviews of any Chicago crime or ghost tour on GetYourGuide, nearly twice as many as the next one, it costs $31, and two hours is the right length for an afternoon or an early evening. You start by the river at 71 East Wacker Drive, walk the South Loop, which was a vice district in the 1920s and 30s, and finish at the Congress Plaza Hotel on Michigan Avenue.
It covers both halves of the name: how Capone ran his business, and the ghost stories attached to the Chicago Riverwalk, Death Alley, the Palmer House and the Congress Hotel. Recent reviewers mention a stop inside the Palmer House to use the restroom or grab a drink or a brownie, and the listing promises a 20-minute break at a famous former gangster hangout.
The Chicago Theatre on State Street, one of the walk's stops. Photo: Empire Tours & Productions, via GetYourGuide.
The one thing it does not cover is the north side. The St. Valentine's Day Massacre site and the Biograph Theater, where John Dillinger was shot, are in Lincoln Park, about three miles north of the Loop. For those, take the bus tour in the comparison below.
Six tours cover Chicago's gangster and true-crime history on GetYourGuide with a real review record. All figures were read on 21 October 2026; prices are per person and every one has free cancellation up to 24 hours ahead.
Ratings are GetYourGuide averages with the review count in brackets. The bus tour recommends a tip of $5 or more per person, in cash or by Venmo; the walks leave tipping up to you.
If the main walk isn't your style, book whichever fits your day:
If you'd rather not walk, or want Lincoln Park
Chicago: Mob and Crime Bus Tour
From $49 · 4.5 ★ (993 reviews) · Chicago Crime Tours and Experiences
An enclosed, climate-controlled coach from 163 East Pearson Street past the St. Valentine's Day Massacre site, the Biograph Theater and Holy Name Cathedral, with short walks off the bus. The bus has five steps and no lift.
Steak, a Chicago hot dog and deep-dish pizza across four stops in River North, plus an old tunnel in a restaurant basement that the listing says Prohibition gangsters used. About a mile of walking.
Prices, ratings and review counts from our 21 October 2026 data check; operators change prices by season and day, so treat them as the shape of the market, not a quote.
04 · The Buildings Behind the Stories
What Is Still Standing, and What Isn't
A gangster tour in Chicago is mostly a tour of absences. The buildings where the Prohibition-era stories took place were hotels, garages and saloons, and many were torn down long ago. Knowing which ones survive tells you what each tour can actually show you.
Gone
The Lexington Hotel, at 22nd Street and Michigan Avenue, was Capone's headquarters from about 1928 until his 1931 conviction. It was demolished in 1995, and a residential tower called The Lex has stood on the site since 2012. Its most famous moment came late: a live television special in 1986 opened a sealed vault in the basement and found nothing of interest.
The garage at 2122 North Clark Street, where seven men were shot on February 14, 1929, in the St. Valentine's Day Massacre, was demolished by 1967. The lot is now a lawn with a few trees next to a nursing home's parking lot, with no marker. The bus tour stops there; on foot, it is a short walk from the Lincoln Park Zoo.
Still standing
The Biograph Theater at 2433 North Lincoln Avenue, where FBI agents shot the bank robber John Dillinger on July 22, 1934, after he left a showing of Manhattan Melodrama. The bus tour has a photo stop there.
Holy Name Cathedral on State Street. On October 11, 1926, the North Side gang leader Hymie Weiss was killed crossing State Street toward his headquarters opposite the cathedral, and stray rounds hit its cornerstone. Some guides say the marks are still visible; treat that as tour lore. The bus tour passes it, and the food walk tells the story.
The Palmer House on East Monroe Street, one of the city's grand hotels and the walk's mid-tour stop, and the Chicago Theatre on State Street, a 1921 picture palace whose marquee is a city landmark. Our walking tours guide covers the Loop's other historic interiors.
Couch Place, the narrow alley ghost guides call Death Alley, runs behind what is now the Nederlander Theatre on Randolph Street. It took the name from the Iroquois Theatre fire of December 30, 1903, in which 602 people died, many of them women and children at a holiday matinee. It is the deadliest single-building fire in American history, and the guides tell it as the tragedy it was.
The walk starts by the river at 71 East Wacker Drive. Photo: Empire Tours & Productions, via GetYourGuide.
Searches for Chicago ghost tours peak in October, and the honest answer is that GetYourGuide's best ghost option is the same Gangsters and Ghosts walk. Its ghost half covers the Riverwalk, Death Alley, the Palmer House and the Congress Plaza Hotel, which local legend calls one of the most haunted buildings in Illinois. The stories most told there involve Room 441 and the 12th floor. They are legends, not documented events, and the guides present them that way.
For a ghost walk on its own, Embers of the Windy City: Chilling Chicago Ghost Tours by US Ghost Adventures is a one-hour evening walk through Lincoln Park, from $27, rated 4.4 from 51 reviews (October 2026). It starts at 7 pm, runs rain or shine and suits all ages. It is a quieter listing: its most recent review dates from September 2025, so book it for the neighborhood rather than the crowd.
Two more options tell darker stories from a different angle. The Historic Gangsters & Twilight Tales Night Cruise on the First Lady fleet tells the Eastland disaster, the Great Chicago Fire and H. H. Holmes from the river at night, from $46. The Chicago Architecture & True Crime Tour by Local Chicago Tours starts at the Palmer House and pairs Loop buildings like the Rookery and the Board of Trade with Holmes and John Wayne Gacy. One reviewer, an architect, gave it 10 out of 10, and the listing says that in rain it stays almost entirely indoors.
Chicago's most famous ghost, Resurrection Mary, belongs to Archer Avenue on the southwest side, far from these routes. None of the downtown walks goes there.
06 · Recent Reviews
What Recent Guests Said About the Walk
Short excerpts from GetYourGuide reviews of the Gangsters and Ghosts walk in October 2026. Guides named in recent reviews include Max, Caroline, Peyton, Tanner and Chris, so yours may differ.
"Great activity on a fall night in Chicago! Peyton was engaging and informative. Tour was interesting and a good length (90 minutes walking) with a stop at the Palmer House to use the restroom, grab a drink, or a homemade brownie."
Guest from the United States · GetYourGuide review, October 2026
"Max did a great job as our guide, with entertaining and educational details enthusiastically delivered at a perfect pace throughout the tour."
Guest from the United Kingdom · GetYourGuide review, October 2026
"Caroline was excellent!! Enthusiastic, energetic, funny and great at story telling."
Guest from Ireland · GetYourGuide review, October 2026
"Chris was great, knew the answers to any and all questions asked not just about the tour but also Chicago in general, would recommend."
Guest from the United Kingdom · GetYourGuide review, October 2026
07 · Honest Fit
Who the Main Walk Suits, and Who Should Pick Another
Book it if
It is your first time in Chicago and you want history told as stories, with Loop landmarks on the way.
You are travelling with children: the listing calls it family-friendly, and children 6 and under go free.
You want gangsters and ghosts in one outing rather than two.
You can walk 1.5 miles at an easy pace, with a break in the middle.
Pick another tour if
You want the St. Valentine's Day Massacre site or the Biograph: take the bus tour.
You have a baby with you: the listing does not recommend the walk for infants.
You use a wheelchair: the listing marks the walk wheelchair accessible but also says it is not suitable for people with mobility impairments, so ask the operator before booking.
You are hoping for a paranormal investigation: this is storytelling, not ghost hunting.
You have luggage with you: large bags are not allowed.
If the first list sounds like you, $31 for two hours is an easy call.
For most visitors it is the Gangsters and Ghosts walking tour by Empire Tours & Productions: two hours through the South Loop, from $31, rated 4.7 from 1,880 GetYourGuide reviews (October 2026), the most-reviewed tour of its kind on the platform. If you want the St. Valentine's Day Massacre site and the Biograph Theater, which are in Lincoln Park, take the Mob and Crime Bus Tour instead: 90 minutes from $49. If you want a meal, the Gangsters and Food Tasting walk in River North includes three tastings for $75.
Yes, if you know what it is. Most of the Prohibition-era buildings are gone, so a gangster tour is a storytelling walk past the places where things happened, not a museum visit. What you pay for is the guide. Recent reviews of the Gangsters and Ghosts walk name the guide almost every time, and the walk also takes you inside the Palmer House and past the Chicago Theatre, so you see Loop landmarks along the way. At $31 for two hours with free cancellation up to 24 hours ahead, it is good value for a first visit.
Yes, though no tour is only about him. The Gangsters and Ghosts walk covers how Capone ran his business in the South Loop, the vice district he controlled in the 1920s. The Mob and Crime Bus Tour adds the St. Valentine's Day Massacre site, and the Gangsters and Food Tasting walk visits an old tunnel used by Prohibition gangsters in River North. His former headquarters, the Lexington Hotel, was demolished in 1995, so no tour can take you inside it.
The Lexington Hotel at 22nd Street and Michigan Avenue, his headquarters from about 1928 until his conviction in 1931. The building was demolished in 1995, and a residential tower called The Lex, completed in 2012, stands on the site. The hotel is best remembered for the 1986 live television special that opened a sealed vault in its basement and found nothing of interest.
In a garage at 2122 North Clark Street in Lincoln Park, on February 14, 1929, where seven men were shot. The garage was demolished by 1967, and the site is now a lawn with a few trees beside a nursing home's parking lot. There is no marker. You can walk past it on your own, and the Mob and Crime Bus Tour includes it.
The best-known mob museum in the United States is the one in Las Vegas. In Chicago, the closest thing on GetYourGuide is the Mob and Crime Bus Tour, whose listing includes a mini mob museum with gangster Frank Nitti's safe and address book, alongside historic video footage shown on the bus.
Yes. He is buried at Mount Carmel Cemetery, 1400 South Wolf Road in Hillside, a suburb west of the city. His marker is a small flat stone near the large family monument. None of the tours on this page goes there, so plan it as a separate trip, and be respectful: it is an active Catholic cemetery.
Resurrection Mary, a young woman in a white dress said to hitch rides on Archer Avenue on the city's southwest side and vanish near the gates of Resurrection Cemetery. The earliest widely cited sighting is from 1939, and folklorists class the story as a vanishing hitchhiker legend. Her identity has never been settled. The downtown walks on this page do not go to Archer Avenue.
Room 441 is the one most often named. The legend is of a woman who appears at the foot of the bed, and some writers say the room inspired Stephen King's story 1408. Other stories attach to the 12th floor, which the Gangsters and Ghosts walk mentions. These are local legends, not documented events. The walk finishes at the Congress Plaza Hotel on Michigan Avenue.
It depends on the tour. The Gangsters and Ghosts walk is family-friendly, and children 6 and under join for free, though the listing does not recommend it for infants. The Embers of the Windy City ghost walk in Lincoln Park says it suits all ages. The Prohibition Speakeasies tour is for adults 21 and over, with adult themes and language.
Yes. The Chicago Architecture and True Crime Tour by Local Chicago Tours covers H. H. Holmes and John Wayne Gacy alongside Loop buildings such as the Rookery and the Board of Trade: two hours from $35, rated 4.9 from 69 reviews (October 2026). The First Lady night cruise also tells the Holmes story from the river. Both handle it as history, without the graphic detail some true-crime media leans on.
A guided visit to bars with a Prohibition story, since alcohol was banned nationally from 1920 to 1933 and Chicago's gangs ran the supply. The Prohibition Speakeasies tour by Prohibition Tours comes as a downtown walk to three bars in the Loop and River North, or a bus tour to four neighborhood bars. It runs 3 to 4 hours from $48, drinks are extra, and it is for adults 21 and over.
Ready for the South Loop's stories?
2 hours · from $31 · 4.7 ★ from 1,880 GetYourGuide reviews (October 2026) · free cancellation up to 24 hours before
Methodology: Tour details, prices, ratings, review counts, routes, suitability notes and review excerpts come from the GetYourGuide listings for tours 234682, 40483, 453097, 419643, 702133, 1007724 and 389179, read on 21 October 2026. Historical facts were checked against Wikipedia's entries on the Lexington Hotel, Hymie Weiss, the Iroquois Theatre fire and Resurrection Mary, the Encyclopedia of Chicago, the Chicago History Museum, CBS Chicago, ABC7 Chicago, History.com and Loop Chicago. Ghost stories are reported as legends.
Last updated: 21 October 2026.
Gangsters & Ghosts walk · 2 hr · from $31Check dates
