Chicago: Gangsters And Ghosts Guided Walking Tour

Join Empire Tours & Productions for a 2-hour guided walk covering gangsters and ghosts in Chicago. Prices start at $31, and the tour holds a 4.7 rating from 1831 reviews.

Overview

This two-hour walking tour covers the Chicago Loop's rougher chapters, from Prohibition-era vice to the ghosts that local legend attaches to several landmark buildings. A historian guide leads the route, which begins near Wacker Drive and ends at the Congress Plaza Hotel. Along the way the group passes the Chicago Riverwalk, the Chicago Theatre, the Palmer House and Cloud Gate, with the guide narrating both documented gangster history and the creepier stories that circulate about each stop.

The walk covers about 1.5 miles in total and includes a 20-minute break at a famous former gangster hangout, so the pace is manageable rather than a march. Stops inside the Congress Hotel and the Palmer House are part of the package. The tone is family friendly, and children aged 6 and under join for free.

It suits visitors who want history delivered with storytelling flair rather than a dry recitation. Recent reviewers consistently praise the guides' knowledge and delivery, with several saying the stories were brought to life. Anyone curious about Al Capone's Chicago, haunted hotels, or the Loop's speakeasy past will get a solid introduction.

What's Included

Itinerary

1. Meet your guideMeet outside Hoyt's Tavern, adjacent to the Royal Sonesta hotel, near 71 E Wacker Drive. There is no hotel pickup for this tour.
2. Chicago RiverwalkThe walk begins along the river, where the guide shares ghost legends said to linger along the water.
3. Chicago Theatre and Palmer HouseStop at two of the city's best known haunted landmarks, with a visit inside the Palmer House included.
4. Cloud Gate and Art InstitutePass by these Loop landmarks as the guide continues the stories of the district's gangster past.
5. Rest stopTake a 20-minute break at a famous former gangster hangout along the route.
6. Congress Plaza HotelFinish with a visit inside the Congress Hotel, described as one of the most haunted places in Illinois, including stories about its 12th floor. The tour ends here.

What To Expect From The Tour

The tour runs on foot for two hours over roughly 1.5 miles, so a little preparation goes a long way.

• Wear walking shoes. Comfortable shoes and clothes are on the operator's bring list, and with good reason given the distance covered. Water is also recommended, especially in warm weather.
• Leave big bags. Luggage and large bags are not allowed on the tour. Travelers planning to join straight from a hotel checkout should arrange bag storage first.
• Guides vary. Reviewers across the board describe the guides as knowledgeable, funny and engaging. Several travelers specifically praised how the guides brought the stories to life and answered questions along the way.
• Expect extras beyond crime. The focus is gangsters and ghosts, but at least one reviewer noted the guide also wove in other Chicago stories, including the invention of the modern brownie. Treat the tour as a general history walk with a dark theme rather than crime only.
• Family friendly. The operator describes the tour as family friendly, and children aged 6 and under can join for free. That said, the listing notes the tour is not recommended for people traveling with infants.
• Bring a tip. Tips are not included in the ticket price and are optional. Having some cash on hand is useful if you want to reward the guide.

Common issues. The listing's own review summary notes that some travelers found guides hard to hear in noisy areas and would prefer slower speech, so standing near the guide at busy intersections helps. Infants are not recommended, and luggage or large bags cannot be brought along. Tips are the only listed exclusion.

Common Questions