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.

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.

Pause at the historic DuSable Bridge, named after Chicago’s first non-Indigenous settler. Learn how this strategic crossing connected the city’s commercial heart and became a silent witness to decades of rapid growth and underworld dealings.

Admire the white terra-cotta façade of the Wrigley Building. As you stand outside, hear how powerful business empires flourished 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.

View the neo-Gothic Tribune Tower, embedded with stones from world landmarks. Your guide will share 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.

Stop 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.

See 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.

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.

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.

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.

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.

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.

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.

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.

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.