Chicago: Gangsters and Ghosts Guided Walking Tour

Set out on a captivating journey through Chicago’s notorious past with the Gangsters and Ghosts Guided Walking Tour. This 2-hour excursion takes visitors into the historic Loop district, uncovering the rise and fall of Al Capone’s criminal empire and encountering eerie tales of ghostly sightings at iconic landmarks. From the Chicago Riverwalk to the grand Palmer House hotel, the tour immerses guests in the city’s dark history, blending stories of gangsters and haunted tales that are sure to leave a lasting impression. Uncover the secrets that have long captivated the city, as you explore the streets where Chicago’s most infamous residents once roamed.

This experience made our list of the 25 Best Guided Tours In Chicago.

Key Points

• Guided walking tour through Chicago’s historic Loop district, revealing the city’s notorious gangster past and tales of haunted landmarks.
• Explore sites central to Al Capone’s criminal empire and discover chilling ghost stories associated with iconic locations like the Palmer House hotel.
• Visit the Chicago Riverwalk, Chicago Theatre, Cloud Gate sculpture, and other landmarks with ties to Chicago’s darker history.
• Learn about the rise and fall of Chicago’s most infamous mobsters and their involvement in extortion, bootlegging, and murder.
• Opportunity to admire the grand architecture and haunted histories of historic landmarks such as the Congress Plaza Hotel.

You can check availability for your dates here:

Tour Overview

This guided walking tour allows visitors to discover the captivating stories of Chicago’s notorious gangsters and eerie ghosts.

It takes participants on a 2-hour exploration through the city’s historic Loop district, delving into its darker past.

The tour provides a unique opportunity to learn about Chicago’s gangster history and the infamous Al Capone’s empire.

Guests will also hear tales of ghosts said to haunt the city’s landmark buildings.

The route includes stops at the Chicago Riverwalk, The Chicago Theatre, Palmer House A Hilton, Cloud Gate, Art Institute of Chicago, and The Congress Plaza Hotel & Convention Center.

With a knowledgeable historian guide, this tour offers an immersive experience into Chicago’s gritty underworld and paranormal lore.

Key Highlights

The tour allows guests to learn about Chicago’s gangster history and the notorious Al Capone’s criminal empire. Visitors will also hear tales of ghosts said to lurk around the city’s historic landmarks during the tour.

Key highlights of the experience include:

1. Discovering the dark past of the Chicago Loop district and learning about Al Capone’s reign over the city’s underworld.
2. Exploring the eerie tales of ghostly sightings at iconic locations like the Chicago Riverwalk, Palmer House, and Congress Hotel.
3. Visiting the sites that were central to Chicago’s gangster era, such as famous hangouts and places associated with the city’s darker history.

Meeting Point and Itinerary

The walking tour begins at the exterior of Hoyts Tavern, right next to the Royal Sonesta hotel, where you will meet their historian guide.

From there, the group will set out on a route through the Chicago Loop district, visiting various locations with ties to the city’s notorious gangster past and haunted history.

The itinerary includes stops along the Chicago Riverwalk, at the iconic Chicago Theatre, the historic Palmer House hotel, the reflective Cloud Gate sculpture, the renowned Art Institute of Chicago, and the Congress Plaza Hotel & Convention Center.

Throughout the 1.5-mile journey, with a 20-minute break at a famous gangster hangout, guests will learn captivating tales about Chicago’s darker legacy.

Gangster History and Haunted Tales

Guests on the Chicago: Gangsters and Ghosts Guided Walking Tour will first learn about the city’s notorious gangster history and Al Capone’s criminal empire.

The tour explores the darker side of Chicago’s past, delving into the rise and fall of some of the city’s most infamous mobsters.

Participants will:

1. Discover how Capone and his gang lorded over Chicago’s underworld, extorting businesses and engaging in bootlegging, prostitution, and murder.

Hear chilling tales of ghosts said to haunt historic landmarks like the Congress Plaza Hotel, where mobsters once conducted their shady dealings.

Visit locations that were once gangster hangouts, learning how the city transformed from a hub of organized crime to the modern metropolitan it’s today.

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Exploring the Chicago Loop

After uncovering the city’s notorious gangster past, the tour moves on to explore the Chicago Loop, the vibrant heart of the downtown area.

This bustling district serves as the backdrop for many of the tour’s captivating stories, from the grand architecture of historic landmarks to the eerie tales of supernatural sightings.

Visitors will stroll along the scenic Chicago Riverwalk, taking in the stunning views of the city skyline. They’ll also visit iconic locations like the Chicago Theatre, the Palmer House, and the Cloud Gate sculpture, known as ‘The Bean,’ which has become a beloved symbol of Chicago.

Throughout the journey, the guide will share fascinating insights into the Loop’s rich history and the supernatural lore that lingers within its streets.

Iconic Landmarks and Hotels

What iconic landmarks and hotels dot the tour’s route through the Chicago Loop? Along the scenic Chicago Riverwalk, visitors can admire the grand architecture of the historic Palmer House and the opulent Congress Plaza Hotel, both renowned for their haunted pasts.

The tour also highlights the beloved Cloud Gate sculpture, affectionately known as ‘The Bean,’ which has become an instantly recognizable symbol of the city.

The tour offers a glimpse into some of the city’s most iconic landmarks:

1. The Chicago Theatre: A stunning 1920s movie palace and performance venue.
2. The Art Institute of Chicago: One of the world’s greatest art museums, housing an impressive collection.
3. The Chicago Riverwalk: A vibrant waterfront promenade offering stunning views of the city skyline.

Inclusions and Exclusions

The tour includes a guided walking experience led by a knowledgeable historian, as well as visits to the iconic Congress Hotel and the legendary Palmer House.

However, tips for the guide are optional, and the tour may not be suitable for those with mobility impairments.

The total walking distance is around 1.5 miles, with a 20-minute break at a famous gangster hangout.

Comfortable shoes, water, and appropriate clothing are recommended.

Children aged 6 and under can join the tour for free, but it’s not recommended for those with infants.

Important Considerations

Participants should be aware that this tour isn’t recommended for people with mobility impairments, as it involves a moderate amount of walking over a 1.5-mile distance.

Plus, the tour isn’t suitable for infants, as the content may not be appropriate for young children. However, children aged 6 and under are welcome to join the tour for free.

To ensure a comfortable experience, attendees are advised to wear:

1. Comfortable, supportive shoes
2. Appropriate clothing for the weather conditions
3. Bring water to stay hydrated

Frequently Asked Questions

Can We Take Photos During the Tour?

Yes, guests are generally permitted to take photos during the tour. However, visitors should be mindful of their surroundings and avoid disrupting the guide or other participants. Certain locations may have restrictions on photography.

Is There Any Special Dress Code for the Tour?

There’s no special dress code for the tour. The guide recommends wearing comfortable shoes and clothes that are suitable for walking. Dressing in layers is also a good idea to prepare for the weather.

Will We Be Able to Sample Any Gangster-Era Cocktails?

Unfortunately, the tour does not include any sampling of gangster-era cocktails. The focus is on exploring the historical sites and learning about Chicago’s darker past through the guide’s narration. Guests will need to seek out separate opportunities to experience those vintage drinks.

How Much Time Is Spent at Each Location?

The tour spends around 15-20 minutes at each location, allowing enough time to explore and learn about the historical significance and ghost stories associated with sites like the Chicago Riverwalk, Palmer House, and Congress Hotel.

Is the Tour Wheelchair Accessible?

The tour is not suitable for people with mobility impairments. It involves 1.5 miles of walking and is not wheelchair accessible. Guests should have good mobility to fully participate in the guided walking experience.

Recap

The Chicago: Gangsters and Ghosts Guided Walking Tour immerses visitors in the city’s captivating history.

Blending stories of notorious gangsters and eerie ghost sightings, the tour takes guests on a 2-hour journey through the Loop district, exploring iconic landmarks and uncovering Chicago’s dark past.

This unique experience offers a thrilling glimpse into the city’s notorious legacy and leaves a lasting impression on all who explore it.

You can check availability for your dates here: