Chicago Gangsters and Ghosts Walking Tour: South Loop History

The South Loop's Violent Past, Told by Someone Who Knows It

A guided walking tour of Chicago's South Loop explores the gangster and ghost stories behind the district's transformation from a vice hub during Prohibition to today's upmarket neighborhood. A historian leads the group through speakeasies, mob hangouts and haunted sites including the Palmer House, Chicago Theatre, and Congress Hotel, with stops at the Chicago Riverwalk and Cloud Gate. The tour runs two hours and includes entry to the Palmer House.

Step-by-step itinerary

Stops and time at each

1. Chicago Riverwalk20m
2. Chicago Theatre20m
3. Palmer House Hilton20m
4. Cloud Gate20m
5. National Portrait Gallery20m

Explore Chicago's gangster and ghost sites

• Walk along Chicago Riverwalk
• Take photo at Chicago Theatre marquee
• Visit Palmer House lobby
• See Cloud Gate sculpture
• View Art Institute of Chicago
• End at Congress Plaza Hotel

The experience

The South Loop wasn't always the polished neighborhood it is now. During the 1920s and 30s, it was the epicenter of Chicago's underworld: underground speakeasies, secret tunnels, bootleggers moving product through the dark. A historian guide walks you through the district's actual geography, pointing out where Al Capone and his associates conducted business, made deals, and partied while the city's laws said they shouldn't exist. The stories are grounded in real places: you'll see the buildings, the corners, the hotel lobbies where these figures operated.

The tour moves along the Chicago Riverwalk, where the dark water itself holds the city's secrets from Capone's bootlegging empire. You'll stop at the Palmer House to step inside its gold-leafed lobby: a masterpiece of Gilded Age opulence that masks a darker history. The Chicago Theatre's iconic six-story marquee gets a photo stop. Cloud Gate, the liquid-mercury sculpture in Millennium Park, anchors another moment. The Art Institute of Chicago, guarded by its bronze lions, carries its own spectral stories. Throughout, the guide connects the physical spaces to the people who moved through them and the legends that linger.

The tour ends at the Congress Plaza Hotel, one of Illinois's most haunted buildings, where Al Capone essentially made his headquarters during Prohibition's height. Two hours covers the route at a walking pace suitable for all fitness levels. The historian guide speaks English and leads a shared group. Wheelchair accessibility is available throughout the district and inside the Palmer House, and strollers are welcome.

What’s included

• Guided walking tour led by a historian.
• entry inside the Palmer House.
• stops at the Chicago Riverwalk, Chicago Theatre, Cloud Gate, the Art Institute of Chicago, and Congress Hotel.

Options for this experience

3 options

Chicago Gangsters and Ghosts TourGuide in English · 11:00, 13:00, 16:00 and 20:00

Halloween Night Special TourGuide in English · 22:00Dare to book? Take part in an exclusive tour late at night during Halloween to discover the area's spooky past once darkness falls, finishing exactly at midnight.

Switch to a Private Tour!Guide in English · 12 departure times: the first at 09:00, the last at 20:00Private Tour: A one-of-a-kind, private outing designed only for your group!

You see the exact price of each option when you check availability.See dates & prices

Before you book

Days and timesEvery day13 departure times: the first at 09:00, the last at 22:00

Book up toStart time

AgesAdult (13 to 64 years) · Senior (65 and older) · Youth (7 to 12 years) · Infant (under 7): free

GroupUp to 25

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends at a different place from where it starts.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated today

Good to know

Easy physical levelWheelchair accessibleAccessible transportStroller friendlyPets welcomePublic transport nearby

Operated by Empire Tours - Chicago

Is this one for you?Book this tour if you want the real stories behind Chicago's Prohibition-era underworld told by someone trained in the history, not a generic ghost walk. The historian guide and the focus on actual mob sites and gangster figures set this apart from tours that lean only on the haunted angle.

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Top questions

Can children come?

Yes. Ticket types: Youth (7 to 12 years); Infant (under 7): free.

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What was the South Loop like during the 1920s and 30s?

The South Loop was Chicago's vice district during Prohibition, home to underground speakeasies, secret tunnels, and bootleggers. Al Capone and other notorious figures used the neighborhood's hotels, streets and hidden spaces to conduct their business and operations.

Do we go inside any of the buildings on this tour?

Yes, the tour includes entry inside the Palmer House, where you'll see the gold-leafed lobby. You'll also stop at the Chicago Theatre, Congress Hotel, and other landmarks, though the itinerary focuses on the exteriors and the stories tied to specific locations.

Who leads the tour and what language is it in?

A historian guide leads the walking tour in English, sharing the true stories of Chicago's gangster past and the ghost legends tied to the South Loop's most famous sites.

How long does the tour take?

The tour runs two hours and covers the South Loop district at a walking pace, with stops at the Chicago Riverwalk, Palmer House, Chicago Theatre, Cloud Gate, the Art Institute, and Congress Hotel.

Is this tour accessible for people with mobility concerns?

Yes, the tour is wheelchair accessible throughout the South Loop district and inside the Palmer House. All areas and surfaces are wheelchair accessible, and infants and small children can ride in a pram or stroller. Service animals are allowed.