Roaring 20’s Happy Hour Tour

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

Join us on our highly entertaining special Friday evening Happy Hour Tour. Begin your weekend while leisurely learning the amazing history of this dynamic era and enjoying some old-fashioned adult beverages! 1920's 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 20's Happy Hour Tour: “Buildings, Booze and Jazz Tour”.

This tour will feature a discussion of Chicago’s Roaring 20's and how this era was symbolized by a building bonanza, gangsters and speakeasies and the cultural influence of Jazz. The 1920's 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 Houlihan's, Cyrano's Cafe 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 20's" Trivia Challenges! Prizes for the winners!

Roaring 20’s Happy Hour Tour Highlights

  • Tour Duration: 3 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!
  • Tour Size Minimum: 8 Guests
  • Maximum: 14 Guests
  • Tours begin at 111 East Upper Wacker - inside Lower Lobby - next to Houlihans Restaurant
  • Please note that while our tours are leisurely strolls, there are numerous stairs along the tour route. Unfortunately, we do not recommend the use of wheel chairs, strollers, canes, walkers etc.
  • 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 became their chosen protectors.



“Roaring Twenties Pub Crawl”

Reviewed June 29, 2014

"This tour attracted me for obvious reasons, but I didn't think it was going to be so much fun and interactive! A trivia contest during the tour, mixed with very interesting history and, of course, drinks and appies at some really cool places along the way made for a very enjoyable evening in Chicago. I would highly recommend this to anyone!"


Calgary, Canada

“History of the Roaring 20's”

Reviewed June 28, 2013

"Even though I have lived in Chicago all of my life I have never taken advantage of some of the things that are offered in the Loop. So, I decided it was about time to do something about it.
While browsing the internet I came across Chicago's Finest Tours. It sounded interesting so I booked it. I met Dan and Sharon a little before our tour was to start. Our group then went to the River Walk. I could have listened to Dan's and Sharon's story telling all evening. The group split into groups for Dan's Trivia questions. Getting the questions right and first gave your team points for great prizes. I thought I new Chicago but I think I came in last. Another surprise was a drink and appetizer at O'Brian's while he continued telling us about how Chicago grew and the characters of that Roaring time."


Chicago, IL