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Walking Tours of Chicago

Chicago is one of the most walkable big cities in the U.S., and its nearly two-century history and many faces—transportation center, agricultural hub, open-air architectural laboratory, Midwest melting pot, Prohibition gangster capital—ensure that there are dozens of walking tours available.

Guided

The Chicago Architecture Foundation (CAF) is the authority for tours of the city’s ever-changing skyscape. CAF’s prime tours include “Historic Skyscrapers,” which looks at 1870s–1930s buildings such as the Art Deco Chicago Board of Trade and Louis Sullivan’s 1899 Auditorium Building, and “Modern Skyscrapers,” which explores the work of post-World War II architects including Mies van der Rohe, whose IBM Plaza and 860-880 Lake Shore Drive helped define modern high-rises. Tours are $15/person plus a $50 group-tour surcharge. Groups must reserve tours in advance.

You can refuel with Chicago Food Planet’s three-hour food-oriented walks through culinary Chicago, including ethnic eateries, specialty food shops and other mouthwatering gastronomic stops. Tours are suitable for all fitness levels and also dabble in Chicago history, culture and architecture.

If you’re ready for a bit of dessert, Valerie Beck’s Chicago Chocolate Tours offers walking and tasting tours of both well-known Chicago chocolate shops and off-the-street boutiques you might not find on your own. Tours include Chocolate Shops of the Loop, the Magnificent Mile and Chicago River, and the Magnificent Mile and Oak Street, plus private Client Entertainment Tours. Fees are $40 per person.


On Your Own

Chicago running great Hal Higdon’s website has a self-guided downtown sculpture tour that’s conveniently close to the Art Institute of Chicago and offers easy directions for how to see (in rapid succession) publicly displayed works by Picasso, Miro, Dubuffet, Chagall, and Calder within just a few blocks of one another.

The pro-free-markets Heartland Institute offers an interesting self-guided walking tour of The Loop. This tour has a definite point of view: how the unbridled capitalism and low government regulation of the past helped make Chicago safer (reversing the Chicago River’s flow helped rid it of disease) and more efficient (the Chicago “El” trains were initially a private venture), and made the Windy City the center of U.S. commodities trading (the Chicago Mercantile Exchange).


For More Info

Chicago Architecture Foundation     312.922.3242     www.architecture.org

Chicago Food Planet     info@chicagofoodplanet.com     www.chicagofoodplanet.com

Hal Higdon    www.halhigdon.com/picasso/walkingtour.htm

Heartland Institute    312.377.4000     www.heartland.org/looptour

Valerie Beck’s Chicago Chocolate Tours    312.863.8614     www.chicagochocolatetours.com

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About the author
Paul Kretkowski