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Walking Tours

Note: I can't believe I really have to say this, but experience has told me that I need to: WALKING TOURS INVOLVE WALKING! There is no way around it: wear comfortable shoes and dress for the weather.

DEARBORN AND VICINITY | Duration: Approximately 2 hours

Dearborn Avenue was the main business drag in early Chicago before Potter Palmer popularized State Street, and this tour provides a trip through the history of Modern American Architecture.

We start with a quartet of beautiful 1890's Chicago School skyscrapers, the elegant Manhattan, Plymouth, Old Colony, and the ornate gothic Fisher Building. We then encounter the historic Monadnock building, a monolithic "missing link" between masonry buildings and the modern steel frame skyscraper. Continuing north takes us into the International-Style Federal Plaza, featuring two Mies Van Der Rohe's classics, the Dirksen and Kluczynski Federal Buildings, counterbalanced by the bright vermillion curves of Alexander Calder's Flamingo sculpture.

The magnificent Marquette Building (another Chicago School masterpiece with arguably the most beautiful lobby in the city) is next, followed by the Inland Steel Building and the Bank One Plaza, which contains Marc Chagall's immense four-sided mosaic "The Four Seasons." We then pass the quirky A-shaped tower of the Bank One Building on the way to Daley Plaza and the famous "Chicago Picasso," Pablo Picasso's untitled steel sculpture which was his gift to the city. Depending on the time, we may also visit the post-modern spaceship building that is Helmut Jahn's State of Illinois Center.

“THE HAROLD ” AND ITS REFERENTS | Duration: Approximately 2 hours

Like dragging out the old vinyl to hear the Parliament records your favorite DJ samples from, we start at the Harold Washington Library, then roll on by all the Chicago School Classics it quotes. The Monadnock, Marquette, Board of Trade, Auditorium, Rookery, and Carson Pirie Scott & Co. buildings are all included.

Then we jump into a time machine and check out Sullivan’s Transportation Building from the Columbian Exposition of 1893! Sorry, just joking about that part…

Even better! We go back to "the Harold" again and see it in the light of the influences it draws upon. A fun frolicking tour that features the old and the new.
BURNHAM-ORAMA | Duration: Approximately 2 hours

The lasting influence of Daniel Burnham (and his firm) on Chicago Architecture will become abundantly clear after this romp around 17 or so of Burnham’s surviving structures in the heart of the downtown. From classics like the Monadnock, Rookery, Reliance, and Fisher to some obscure but lovely edifices like the Heyworth, Edison and Conway buildings; this peripatetic perambulation (combined with my “Oh so trenchant and entertaining” panoply of facts and anecdotes) will leave you awed by the scope of Big Dan’s Vision. It can even become an Urban Hike if you want to march on down to the Field Museum!

MOSAICS IN THE LOOP | Duration: Approximately 2 hours

This walking tour starts at the Cultural Center for a dive into their ocean of Tiffany tile and glass, then a peek into the original Marshall Field & Co. on our way to LaSalle Street for a gander at Roger Brown’s rendering of Daedalus and Icarus. We circle around Chagall’s stunning 4-sided leviathan "The Four Seasons" in the Bank One Plaza a few times before finishing up at the Marquette building with its jaw-dropping array of figures rendered in Tiffany splendor.

MILLENNIUM PARK | Duration: 2 hours

Check out Chicago's 21st Century gem of a park! The Peristyle, Crown Fountain, Lurie Gardens, the Frank Gehry-designed amphitheater and pedestrian bridge, and Anish Kapoor's revelatory sculpture, Cloud Gate (instantly nicknamed "The Bean", it's already a Chicago favorite)—basically the whole darn thing is included in this scintillating jaunt.

Time: 2 Hours. Depending on if you're in a hurry or want to dawdle and dip your toes in the fountains.

GRANT PARK | Duration: 2 hours

Known as "Chicago's Front Yard", this 300-plus acre park is home to fabulous sculpture and some of the most stunning floral beds and landscaping you're going to find anywhere. Not to mention Buckingham Fountain, the gigantic Chicago landmark that has delighted millions throughout the years.

Time: 2 Hours. (See the Urban Hikes page if you're interested in a longer tour of Grant Park.)

NAVY PIER RAMBLE | Duration: 2 hours

“Take a long walk on an extremely long Pier,” is the watchword of the day on this trek to the end of one of Chicago’s most popular attractions. Derided by many as a tourist trap, there’s still a ton of cool stuff on this ¾ mile pile of bricks and pylons, and it can’t be beat as a people-watching venue. This could be a quick jaunt or an all-day odyssey depending on how much and where you want to linger. Be sure to bring a camera for the awesome views of lake and skyline!

Walking Tour Rates

Two-Hour Walking Tours- $25 per person (5-person minimum, 25-person maximum.)

Page last updated: 18 August 2009


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