Here are the top recommended Chicago running routes from the
national runners travel guide
Fun on Foot in America's Cities:

Chicago - Lakeshore North - Navy Pier to Wrigleyville
One of the top running routes or walking routes anywhere!  Experience the
natural beauty of the Lake Michigan shore, together with the attractive
parkland setting of Lincoln Park for most of the way.  There are beaches,
monuments, marinas, and open spaces.  Running and walking conditions
are excellent.  End near legendary Wrigley Field, home of the Cubs.  In
Wrigleyville there are many options for eating, drinking, and entertainment,
and a convenient subway ride back downtown.

Chicago - Lakeshore South - Navy Pier to Hyde Park
More of the natural beauty of Lake Michigan, with a variety of scenery and
sights all along the Chicago lakeshore trail.  Pass Grant Park, Soldier Field,
McCormick Place, Burnham Park, and some popular beaches.  End near
Jackson Park (site of the famous Columbian Exposition of 1893), the
acclaimed Museum of Science and Industry, and the University of Chicago.  
There is express bus service back to downtown Chicago.

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Lakeshore North Trail
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Information, maps and books for runners and walkers
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plan exciting Chicago running routes, walking routes
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For full commentary, maps, and directions see  
Fun on Foot in America's Cities - the runners'
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book also covers running, walking in 13 other
major US cities.
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