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Chicago Gangsters and Ghosts Walking Tour 2 hr

TourTruth score 8.3 out of 10

Very goodTop 14% in Chicago

69 reviews · Rated on 1 provider · How we score

  • Chicago
  • 2 hrs
  • Updated November 4, 2026

Follow Al Capone’s trail and hear chilling legends on a guided 2-hour walk through downtown Chicago’s storied landmarks.

About this tour

Chicago’s shadowy history comes alive on a guided walk through downtown, where Prohibition-era crime and eerie legends linger among landmark buildings. Follow the stories of gangsters and ghosts with a licensed guide who connects the city’s famous sights to its darker past.

This 2-hour Chicago Gangsters and Ghosts Walking Tour begins near the Riverwalk and traces Al Capone’s rise through tales of bootlegging, rivalries, and the gang wars that shaped Michigan Avenue. Along the way, pass the Chicago Theatre and Palmer House as your guide shares crime lore and haunted stories tied to the city’s history. The route continues toward Cloud Gate and ends at the Congress Plaza Hotel, a landmark associated with unsettling tales. Expect local perspectives and commentary that bring downtown’s cultural history into the story, with time to ask questions as you walk.

The tour covers about 3 km on foot, so wear comfortable shoes and dress for the weather. Meet outside the Hyatt Regency Chicago, then step into a side of the city that’s easy to miss from the sidewalk alone. Book your Chicago Gangsters and Ghosts Walking Tour to explore the stories behind the skyline.

Highlights

  • Trace Al Capone’s rise from the Riverwalk to the Congress Plaza Hotel
  • Hear how Prohibition-era gang wars shaped Michigan Avenue
  • Explore crime lore around the Chicago Theatre and Palmer House
  • Discover ghost stories at Congress Plaza Hotel
  • See Cloud Gate and downtown landmarks on a guided walk

What's included

Included

  • 5-Star Licensed Guide
  • Guided walking tour of downtown Chicago highlights and hidden gems
  • Commentary on Prohibition-era crime, infamous mobsters, haunted legends, and Chicago’s cultural history
  • Local perspectives and recommendations for the Riverwalk, Michigan Avenue, and surrounding areas
  • Applicable taxes and service fees

Not included

  • Food and drinks
  • Transportation

Ratings on each provider

The ratings and review counts each booking site shows for this tour.

What reviewers mention

Themes that come up most in this tour's reviews.

Important information

  • Arrive 10 minutes early; late arrivals are nonrefundable
  • Meet outside the main entrance of Hyatt Regency Chicago, 151 E Wacker Dr; do not enter the hotel
  • The closest subway station is State/Lake, about a 10-minute walk; the nearby bus stop is Wacker (Upper) & Columbus
  • The route covers approximately 3 km (1.8 miles) on foot and is not suitable for people with reduced mobility
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  • Wear comfortable shoes and dress for the weather
  • Pets, baby strollers, suitcases, and scooters are not permitted
  • Commentary is provided in one language only; check your phone and email for operator updates

Frequently asked questions

How long is the tour?

The walking tour lasts 2 hours and covers approximately 3 km (1.8 miles).

What languages are available?

Live commentary is available in English or Spanish, with one language used per tour.

Where is the meeting point?

Meet outside the main entrance of Hyatt Regency Chicago at 151 E Wacker Dr. Do not enter the hotel.

How large is the group?

The tour has a maximum of 25 participants.

Can I cancel for free?

Free cancellation is available up to 24 hours before the tour.

How this score is calculated

This score is based on one provider. GetYourGuide rates it 4.78 from 69 reviews. We place that rating among all GetYourGuide ratings and weight it by its review count. If the tour is found on another provider later, both ratings are combined.

How the score works and rating distribution in Chicago
  • Each provider rating is turned into a percentile: the share of that provider's ratings it beats, weighted by review counts.
  • Listings on different providers are combined in proportion to their review counts.
  • Tours with few reviews are pulled toward the average until more reviews come in, so a handful of perfect reviews can't top the list.
  • The result is shown from 0 to 10: this tour scores 8.3. Top 14% in Chicago means it ranks in the top 14% of tours in Chicago by this score.

Provider rating distribution in Chicago

How many tours in Chicago have a provider rating at or below each value. The dashed line is this tour.

  • GetYourGuide
  • Viator

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