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Chicago History Tour Plus

Chicago's Finest Tours

Weekly Event - Every Thursday Saturday & Sunday: 1:00 PM to 3:30 PM (CDT)

Chicago History Tour Plus

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Event Details

Chicago History Tour Plus

History and entertainment at its best!


The “story” of Chicago is an amazing account of how a swampland located at the intersection of a lazy prairie river and Lake Michigan transformed into one of the world’s leading “Alpha” cities. Listen as our tour guides thoughtfully describe those forging events that help shaped the city in to perhaps one of the most beautiful cities in the world.

Enjoy viewing the numerous archival photos and listen closely to our guides stories that were each chosen specifically to bring Chicago’s history to life right before your eyes.

Plus - guests finish the tour with a short boat ride along the Chicago River and observe some of Chicago's iconic buildings!

Chicago History Tour Plus Highlights

  • Tour Duration: 2 and ½ hrs – med. walk - 1 mile & 1/2
  • Tours are conducted along scenic Chicago River Walk
  • Tours begin on June 4 and are offered every Wednesday, Saturday & Sunday at 1:00 pm
  • Minimum: 4 Guests
  • Spectacular views of Chicago’s iconic skyline
  • Entertaining stories featuring the Fort Dearborn Massacre, Great Chicago Fire, 1893 World’s Fair, Burnham Plan, Union Stockyards and so many more
  • Tours begin at 111 East Wacker - inside Lower Lobby - next to Houlihans
  • After a 10 minute boat ride along the Chicago River, tour ends near Wrigley Building - 400 North Michigan - diagonally across the river from where tour began
  • Plenty of places to sit and relax in the sun or shade
  • Learn about Chicago’s most fascinating characters including the architects, millionaires, vice figures and politicians
  • Trivia contest

The History of the “Second City”

Did you ever wonder why Chicago is called the “Second City”? Most people believe that for decades that it was called such because Chicago was in fact second in population to New York City. However, the real reason for this moniker is because we built our city basically from ground up after the Great Chicago fire of 1871, and thus, we are the second version of this great city! If you are interested in learning more about Chicago from its early risings to its current standing as one of the world’s great cities, please join us for an entertaining and informative walking excursion along the city’s River Walk! Did Mrs. O’Leary’s cow really start the Great Fire? You will find the answer to that question and so many more by joining us Chicago’s Finest River Walk History tour!

Have questions about Chicago History Tour Plus? Contact Chicago's Finest Tours


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

Weekly Event - Every Thursday Saturday & Sunday: 1:00 PM to 3:30 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 tripadvisor.com. I hope you join us soon on one of our amazing journeys! Respectfully, Dan O’Connell

Please give us a call to make your reservation after purchasing a ticket:


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