Experience the Windy City in a different perspective — from the past — on this 3-hour walking tour that dives into why Chicago was such a powerhouse during the Roaring '20s. Visit popular vintage venues, such as the Chicago Theatre, where famous jazz musicians performed. Learn about the city’s booming history, including its link to prohibition, women’s suffrage, flappers, and even gangsters.
3-hour Roaring '20s walking tour in Chicago
Spot vintage venues, such as the Chicago Theatre and the Chicago Motor Club building
Learn about the city’s history of prohibition, women’s suffrage, flappers, and gangsters
See places where people enjoyed listening to jazz music during the 1920s
Pass by the Hard Rock Hotel, Virgin Hotel, and the InterContinental Chicago
Please note this tour includes a moderate amount of walking
For this 3-hour Roaring ‘20s tour in Chicago meet in front of Potbelly Sandwich Shop at State Street and Lake Street a little before 1p.m. Your tour will take off right at 1p.m., so make sure not to be late.
First your guide shows you to the Chicago Theatre, where he or she fills you in on the history of the venue, and tells you stories of a few of its popular 1920s jazz performers. Then its off to the North side of the city. Your guide explains why many people, including Al Capone, considered the city a main hub of the decade. Learn about how prohibition, women’s suffrage, flappers, and even gangsters affected Chicago.
Pass other hotspots, including Hard Rock Hotel, Virgin Hotel, and the InterContinental Chicago before making your way to Harry Caray’s Italian Steakhouse on West Kinzie Street. Your tour guide leaves you here, and you can continue exploring on your own if you choose.