Chicago History Tour

History at its best!

Chicago History Tour begins at 1:00 pm sharp on Saturdays at the Hyatt Regency Hotel - 151 East Upper Wacker - inside main lobby next to concierge desk. The tour group will immediately engage Chicago's indoor Pedway system. The Pedway (Pedestrian Walk-Way) spans nearly 5 miles in length and it is an assortment of underground corridors, building concourses, food courts, train stations and sky-bridges. It is the city’s secret weapon against the realities of Chicago’s harsh winter.

During this “Urban Safari”, guests learn about the history of Chicago and by use of our special tour map, navigate nearly 1 and ¼ miles of this unique urban terrain. Along the way, guests will enjoy stops at some of Chicago's best historical destinations including; Chicago Cultural Center, Macy's Department Store, Daley Center, City Hall and the Thompson Center.

At the Cultural Center, guests will view the world's largest Tiffany Dome while listening to stories about the Tiffany family of New York. Only one block away guests will view the world's largest Tiffany Ceiling in Macy's Department Store. The Daley Center is replete with stories of Chicago's past and present not to mention the spot leading to the demise of the infamous "Blues Mobile" featured in the "Blues Brothers" movie. City Hall's lobby is not only breathtaking but hurried and full of bustle as politicians make their way to and from the Mayor's office or Chicago City Council Chambers located on the second floor. And lastly, the tour concludes in Helmut Jahn's crown jewel - State of Illinois Building - 100 West Randolph.

History stories featured on the tour include some of the following; Marquette & Joliet, Jean Baptiste Pointe du Sable,Fort Dearborn Massacre, 1848 - "Annus Mirabilis", Illinois & Michigan Canal, raising Chicago, Chicago Watertower, Chicago shipping and Sanitation Canal, Union Stockyards, Great Chicago Fire, skyscrapers and architecture, 1893 World's Fair, S.S. Eastland Disaster, Burnham Plan and so much more.

All tours include a intermission restroom stop and treat along the way!

Chicago History Tour Highlights

  • Tour Duration: 2 and ½ hours – minimal walking
  • Please be advised, while these tours are conducted in Chicago’s indoor heated Pedway, these tours do not go into any detail about the use or history of the Pedway. If you are interested primarily in learning about the Pedway, please refer to our Pedway Explorers Tour.
  • History Tours begin at the Hyatt Regency Chicago - 151 East Upper Wacker - inside main lobby near Concierge desk and end at 35 West Wacker.
  • Please dress accordingly - although most of the tour takes place inside the heated Pedway, outside walking for a few minutes at a time is part of the tour.
  • Tours are held every Saturday at 1:00 pm - minimum walking.
  • FITBIT STEPS: 4,800
  • 48 hour cancellation policy.
  • Minimum: 4 guests
  • Hear entertaining stories featuring the Fort Dearborn Massacre, Great Chicago Fire, 1893 World’s Fair, Burnham Plan, Union Stockyards and so many more!
  • Plenty of places to sit and relax while listening to great storytelling.
  • 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 “alpha” cities, please join us for an entertaining and informative walking excursion along the city’s indoor heated Pedway! 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 History Pedway Tour!


“Outstanding 'History' Tour!”

5 of 5 stars - reviewed March, 2016

"The Chicago History Tour is highly recommended. Our excellent guide Dan was energetic, entertaining, and provided an informative interactive experience. Great overview of Chicago's history, and a good opportunity to experience the little known Pedway. Easy walking, stopped and sat a few times listening to Dan's wonderful knowledge, and even had a few bathroom breaks if needed. A very fun afternoon. This tour is great for visitors and natives alike."

Kim K

Chicago, IL