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Roaring 20's Pub Crawl

Chicago's Finest Tours

Weekly Event - Every Friday: 5:00 PM to 7:30 PM (CDT)

Roaring 20's Pub Crawl

Event Details

Roaring 20’s Pub Crawl

“Tis here we pledge perpetual hate, to all that can intoxicate…”


Join us on our highly entertaining Friday evening Pub Crawl. Begin your weekend while leisurely learning the amazing history of this dynamic era and enjoying some old-fashioned adult beverages! 1920s Chicago was the place to be! The horizon was filled with new skyscrapers reaching for the heavens, the town was “dry” but no one went thirsty and the nighttime air was thick with laughter and the cool sound of Jazz! Sound interesting? Please join us on our Roaring 20s Pub Crawl: “Buildings, Booze and Jazz Tour”.

This tour will feature a discussion of Chicago’s roaring 20s and how this era was symbolized by a building bonanza, gangsters and speakeasies and the cultural influence of Jazz. The 1920s were an age of seismic social and political change and no other city shined brighter than the “Windy City” during this tumultuous era in America! Stops include Houlihans, O'Briens River Walk Café and the inimitable Harry Caray's.

First drink and appetizers are on our us!

Come prepared to compete in our one-of-a-kind "Roaring 20s" Trivia Challenge! Prizes for the winners!

 Roaring 20’s Pub Crawl Highlights

  • Tour Duration: 2 and ½ hours – minimal walking
  • Tours are conducted along the Chicago River.
  • Please understand this is not a Chicago “Gangster” Tour
  • First Drink and appetizers are on us!
  • Tours begin on June 6 and are offered every Friday at 5:00 pm.
  • Minimum: 6 Guests
  • Maximum: 14 Guests
  • Tours begin at 111 East Wacker - inside Lower Lobby - next to Houlihans Restaurant
  • Tours end at Harry Carays - 33 West Kinzie
  • Spectacular views of Chicago’s iconic skyline.
  • Entertaining stories featuring the rise of Chicago’s skyscrapers, the Volstead Act and how organized-crime seized control of a city, and of course, all that Jazz!
  • Plenty of places to sit and relax in the sun or shade.
  • Learn about Chicago’s most incredible legends including; “Jelly Roll” Morton, Tony Jackson, Louis Armstrong, Al Capone and so many other characters brought to life.
  • Trivia Contest

“Buildings, Booze & Jazz”

Learn how the 18th Amendment gave birth to Chicago’s infamous bootleggers, racketeers, and organized crime figures such as “Bugs” Moran and Al Capone. Did the term “Underworld” actually develop in Chicago? Did the newspaper “circulation wars” in the preceding decade actually give rise to organized crime in the city? Learn the answer to those questions and so many others on this tour. View and learn all about the iconic buildings constructed in the 1920s including the Wrigley, Tribune, Mather tower, Carbide & Carbon Intercontinental Hotel and so many more. Discuss how the “Great Migration” from the south to the north spawned the Jazz age and countless famous musicians and why the city’s gangsters who ruled the city at this time were their chosen protectors.

Have questions about Roaring 20's Pub Crawl? Contact Chicago's Finest Tours


Lower lobby — across from Houlihan's Restaurant
111 E Upper Wacker Dr
Chicago, IL 60601

Weekly Event - Every Friday: 5:00 PM to 7:30 PM (CDT)

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Chicago's Finest Tours

Welcome! My name is Dan O’Connell and I am the founder of Chicago’s Finest Tour. I began this business 3 summers ago for one reason – to tell "the" story. In short, to tell the amazing story of Chicago - how a mere swampland located at the intersection of a lazy prairie river and Lake Michigan became one of the world’s leading “Alpha Cities”! Like any great novel, the “Chicago Story” has many chapters and each one of our tours are thoughtfully designed to tell one or many chapters of this incredible saga! The tour guides of Chicago’s Finest Tours love to narrate this inimitable account of the “Windy City”. Our tour guides are enthusiastic, energetic and above all, entertaining. If you think a history tour and entertaining are contradictory, I encourage you to try one of our tours. Like the thousands of guests we have entertained thus far, you will too will find that a history tour can be both informative and entertaining. If you don’t believe me, please check out what hundreds of our guests have to say about their tour experience with us on I hope you join us soon on one of our amazing journeys! Respectfully, Dan O’Connell

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