Welcome! My name is Dan O’Connell and I am the founder of Chicago’s Finest Tour. I began this business 5 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

Cancellation Policy: Failure to provide at minimum 48 hours cancellation notice results in cash deposit and/or voucher forfeiture.

Reservations are required. To make reservations please call us or email us below and leave a message with your name, phone number, email address, voucher code (groupon-8 capital letters, living social-begin with 1000 and travel zoo -4 digit pin number) and what day and time you would like to take our tour. One of our representatives will contact you and confirm your reservation. Summer tours are held rain or shine. Attendance typically fills up quickly and is limited to 20 people per tour so advance reservations are a must!