Being in the country's third largest city (population: 2,695,598) means you have a lot of territory to wrap your brain around. Start by taking time to get an overview. Choose a tour that caters to your interest.
Loop Tour Train A ride on the El (pictured) illustrates why Chicago's heart is called The Loop--the tracks lasso the city's financial heart. Get a special deal on Saturdays, May through September, if you're able to snag a free ticket from the Chicago Cultural Center at Randolph and Michigan. The transit authority also has a downloadable sightseeing guide. transitchicago.com
Chicago Greeters Volunteers lead free two- to four-hour neighborhood walking tours. Choose from more than 25 neighborhoods and 40 interests, including fashion, film, ethnic and public art. chicagogreeter.com
Bobby's Bike Hike Offers guided bike tours of neighborhoods, a great way to learn more about the city's history. bobbysbikehike.com
Seadog Zip along on a speedboat while a stand-up comic leads an informative architectural tour. seadogcruises.com
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