• Hyatt Regency Chicago - Meet your Licensed Guide outside the Hyatt Regency Chicago at 151 E Wacker Dr, near the main entrance facing Wacker Drive. The hotel is a 10-minute walk from the State/Lake CTA station and close to several Michigan Avenue bus stops. Please wait by the entrance and arrive 10 minutes early.
• Chicago Riverwalk - Start your journey along the Chicago Riverwalk, where gleaming towers rise above waters once linked to Prohibition smuggling routes. Your guide will narrate the city’s evolution from a frontier outpost to a crime capital, setting the scene for the rise of Al Capone and organized crime.
• DuSable Bridge - Stop at the historic DuSable Bridge, named after Chicago’s first non-Indigenous settler. Discover how this strategic crossing connected the city’s commercial core and became a silent witness to decades of rapid growth and underworld activities.
• Wrigley Building - Admire the white terra-cotta façade of the Wrigley Building. As you stand outside, learn how powerful business empires thrived during the same era that mob bosses tightened their grip on Chicago’s streets. Note: Attraction visit will be available from the exterior. No option of going inside the attractions.
• Tribune Tower - Observe the neo-Gothic Tribune Tower, embedded with stones from world landmarks. Your guide will explain how media influence and sensational headlines shaped public perception of gang violence in the 1920s. Note: Attraction visit will be available from the exterior. No option of going inside the attractions.
• The Chicago Theatre - Pause beneath the iconic Chicago Theatre marquee. From the sidewalk, discover how this 1921 landmark became a symbol of glamour during Prohibition, when jazz, entertainment, and organized crime thrived side by side. Note: Attraction visit will be available from the exterior. No option of going inside the attractions.
• Marina City - View the striking twin towers of Marina City. Learn how Chicago reinvented itself architecturally after its most turbulent decades, rising from corruption and chaos into a modern metropolis. Note: Attraction visit will be available from the exterior. No option of going inside the attractions.
• House of Blues Chicago - Outside House of Blues, hear about the city’s deep musical roots and how blues culture grew from hardship, migration, and the same neighborhoods once influenced by gang activity. Note: Attraction visit will be available from the exterior. No option of going inside the attractions.
• Palmer House a Hilton Hotel - Stand before the historic Palmer House Hilton and uncover its ties to political power, celebrity guests, and chilling tales that fuel its haunted reputation. Your guide will separate documented events from enduring local lore. Note: Attraction visit will be available from the exterior. No option of going inside the attractions.
• Millennium Park - Walk through Millennium Park, a public gathering space that represents Chicago’s rebirth. Discover how this area evolved from rail yards to one of the city’s most visited landmarks.
• Cloud Gate - Pause at Cloud Gate for photos beneath its mirrored surface. As the skyline reflects around you, hear how Chicago rebuilt itself after fire, crime waves, and economic upheaval.
• The Art Institute of Chicago - View the grand exterior of the Art Institute of Chicago. Learn how art, wealth, and philanthropy shaped Michigan Avenue while the city balanced refinement with a rough-edged past. Note: Attraction visit will be available from the exterior. No option of going inside the attractions.
• South Michigan Avenue & North Michigan Avenue - Stroll along Michigan Avenue, once patrolled by figures linked to bootlegging networks. Your guide will connect luxury storefronts and historic façades to the money that flowed through Chicago during Prohibition.
• Grant Park - Pass through Grant Park, often called “Chicago’s front yard.” Discover how public gatherings, protests, and celebrations unfolded here against a backdrop of political tension and social change.
• The Congress Plaza Hotel & Convention Center - Conclude outside the Congress Plaza Hotel, long associated with ghostly sightings and infamous guests. Hear accounts that built its haunted reputation and reflect on the city’s lasting fascination with crime and the supernatural as your 2-hour experience comes to an end. Note: Attraction visit will be available from the exterior. No option of going inside the attractions.

• Gangsters and Ghosts Walking Tour of Downtown Chicago
• Local perspectives and recommendations for the Riverwalk, Michigan Avenue, and surrounding areas
• Commentary on Prohibition-era crime, infamous mobsters, haunted legends, Chicago’s cultural history
• 5-Star Licensed Guide
• All applicable taxes and service fees

• Food and drinks
• Transport
• Entrance to all attractions

Explore the birthplace of a nation and delve into the narrative of America’s quest for independence. Embark on a 2.5-hour guided tour along the Freedom Trail with Rosotravel, designed for travelers seeking insight, emotion, and connection—not just photographs.

Commencing at Boston Common, a Licensed Guide will animate history at landmarks such as the Massachusetts State House, Old South Meeting House, Old State House, Faneuil Hall, and Old North Church, concluding near the Bunker Hill Monument.

Through engaging storytelling and expert insights, uncover the individuals and events that forged a nation. Don’t just visit Boston—comprehend it. Reserve your walking tour today.

Uncover Chicago’s shadowy history with a 5-Star Licensed Guide downtown. Follow Al Capone’s ascent from Riverwalk to Congress Plaza Hotel. Discover how Prohibition-era gang conflicts influenced Michigan Avenue’s legacy. Visit Chicago Theatre and Palmer House, steeped in crime lore. Experience the eerie atmosphere at Congress Plaza and Cloud Gate at night.

• It’s best to arrive 10 minutes in advance, as late arrivals are nonrefundable. Check your phone and email for important information from Rosotravel, your tour operator
• This walking tour covers approximately 3 kms (1,8 miles) on foot and is not suitable for people with reduced mobility.
• Wear comfortable shoes and dress appropriately for the weather: rain, hail or sunshine!
• Please don’t bring pets, baby strollers, suitcases and scooters.
• Commentary will be offered 1 language only.
• Maximum 25 participants.

For a full refund, cancel at least 24 hours before the scheduled departure time.