Chicago Congress Plaza Walking Tour
Overview
Available languages
2 hours
Mobile ticket
Walk where a nation was born and experience the story behind America’s fight for independence. Join Rosotravel for a 2.5-hour guided walk along the Freedom Trail, crafted for travelers who want insight, emotion, and connection—not just photos.
Starting at Boston Common, your Licensed Guide brings history to life at sites including the Massachusetts State House, Old South Meeting House, Old State House, Faneuil Hall, and Old North Church, ending near the Bunker Hill Monument.
Through vivid storytelling and expert perspective, discover the people and events that shaped a nation. Don’t just visit Boston—understand it. Book your walking tour today.
Discover Chicago’s dark past with a 5-Star Licensed Guide downtown
Trace Al Capone’s rise from Riverwalk to Congress Plaza Hotel
Learn how Prohibition gang wars shaped Michigan Avenue’s legacy
See Chicago Theatre and Palmer House tied to crime lore
Feel chills at Congress Plaza and Cloud Gate at night
Additional Info
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Not recommended for travelers with spinal injuries
Not recommended for pregnant travelers
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
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.
What To Expect
Meet your Licensed Guide outside the Hyatt Regency Chicago at 151 E Wacker Dr, near the main entrance facing Wacker Drive. The hotel is 10-min walk from the State/Lake CTA station and close to several Michigan Avenue bus stops. Please stand by the entrance and arrive 10 minutes early.
Chicago Riverwalk
Begin along the Chicago Riverwalk, where glittering towers rise above waters once tied to Prohibition smuggling routes. Your guide will introduce the city’s transformation from frontier outpost to crime capital, setting the stage for the rise of Al Capone and organized gangs.
Options
USCH006 2 - Hour English
Ghosts & Gangsters of Chicago Licensed Guide
USCH006 2 - Hour Spanish
Ghosts & Gangsters of Chicago Licensed Guide
What‘s Included
Gangsters and Ghosts Walking Tour of Downtown Chicago Highlights and Hidden Gems
All applicable taxes and service fees
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
Food and drinks
Transport
Entrance to all attractions
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Secure Checkout
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Operated by New York City Tours