Chicago’s #1 History Tour

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.

Come explore with us the newly expanded River Walk. Opening 2016, 3 new "rooms" (Water Plaza, Jetty & Boardwalk) all promise to make the River Walk even more fun and the place to be!

Tours begin at Peet's Coffee & Tea - Wrigley Building Plaza - 400 North Michigan Avenue - across from Walgreen's.

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

Chicago’s #1 History Tour Highlights

  • Tour Duration: 2 and ½ hrs – med. walk - 1 mile & 1/4
  • Tours are conducted along scenic Chicago River Walk
  • Tours begin on May 27 and end October 28 and are offered every Saturday at 1:00 pm
  • Tour Size Minimum: 4 Guests
  • 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.
  • 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 Peet’s Coffee & Tea - Wrigley Building Plaza - 400 North Michigan
  • After a 10 minute boat ride along the Chicago River, tour ends near Wrigley Building Plaza - 400 North Michigan
  • 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”

Visited August 2015Did 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!


“Great, informative tour”

Reviewed June 20, 2016

"We really enjoyed this tour. It is fast paced and we learned a lot about Chicago's history in such a short time. It was a good time. We did get a bathroom break half way through the tour which was nice. Wear comfortable shoes and be ready to answer trivia questions for a shot at a Starbucks card. That made it fun for everyone. Our guide was great."


Chicago, IL


“Wonderful Tour!”

Reviewed August 31, 2015

"We loved the History Tour Plus along the beautiful Riverwalk with Richard Zieman, a Chicago native. He was informative as well as humorous. Had great facts and anecdotes as well as a booklet with more information. Also had gift cards for Trivia questions correctly answered."

Jill W

Mishawaka, IN


“History Walking Tour”

5 of 5 starsReviewed September 23, 2014

"On Sunday, September 6, I took the history walking tour with Rick as our tour guide. It was a fantastic tour on a fantastic day (can't promise, however, that the weather is always as favorable, although Rick told us it was 72 degrees with low humidity 365 days a year in Chicago -- that was one element of the tour he may have exaggerated just a smidge.). Rick was a knowledgeable and engaging leader. I appreciated that he made it an interactive experience, asking us questions and offering a few little prizes for correct responses. As a hearing impaired person, I was also appreciative that he spoke loudly and clearly. I heard every word! I would recommend this tour without hesitation. While we walked a fair distance in the 2.5 hours, there were plenty of opportunities to stop and sit, and I would not call it strenuous at all. Bravo to Chicago's Finest Tours. Well done!"

Janis N

Reading, Massachutes


“Chicago History Tour Rocks”

Reviewed September 7, 2014

"One of the best tours ever! Our guide, Rick, took us along the River walk and pointed out buildings and their history with stories of events and unknown facts. He was well versed and kept us intrigued while making it fun and entertaining. We each got a booklet with pictures to guide us through the various areas and events ( we had to return them after the tour. My husband wanted to buy one!). A definite don't miss for tourists and Chicagoans alike!"


Grayslake, IL