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Chicago’s architecture is world-famous. Luckily, the Chicago Architecture Center offers first-rate guided tours to help visitors understand what makes this city’s skyline so special. Start inside their new center, where exhibits include a Skyscraper Gallery featuring scale models of some of the world's most iconic buildings, as well as another meticulous scale model of Chicago with tiny replicas of 3,000 buildings. Lights and film projections use the model to recount the history of the city's architecture from the rebuilding period following the Great Fire up to Chicago's current status as a world leader in innovative skyscraping.

The foundation offers walking, bike, boat, Segway, El, and bus tours to more than 80 architectural sites and environments in and around Chicago, led by nearly 450 trained and enthusiastic docents (all volunteers). I highly recommend taking at least one CAC tour while you’re in town—each one will help you look at (and appreciate) the city in a new way. Tours are available year-round but are scheduled less frequently in winter.

One of the CAC’s most popular tours is the 1 1/2-hour Architecture River Cruise, which glides along both the north and the south branches of the Chicago River. Although you can see the same 50 or so buildings by foot, traveling by water lets you sit back and enjoy the buildings from a unique perspective. The excellent docents provide interesting historical details, as well as some fun facts. (David Letterman once called the busts of the nation’s retailing legends that face the Merchandise Mart the “Pez Hall of Fame.”) The docents do an applause-worthy job of making the cruise enjoyable for visitors with all levels of architectural knowledge. In addition to pointing out buildings—Marina City, the Civic Opera House, the Willis Tower—they approach the sites thematically, explaining, for example, how Chicagoans’ use of and attitudes toward the river have changed over time.

In the summer (late May–mid Oct), cruises run on the hour or half hour (check website for times); the cost is $44.48 per person ($49.48 cruise + CAC admission). The trips are popular in the summer, so I’d definitely purchase tickets in advance online if you’re hoping for a particular date or time.

If you have a limited amount of time in Chicago and want to squeeze in a lot of sightseeing, try the Highlights by Bus tour, a 3 1/2-hour overview that covers the Loop, Hyde Park—including a visit to the interior of Frank Lloyd Wright’s Robie House—and the Gold Coast, plus several other historic districts. Tours start at 9:30am on Saturdays (check website for exact dates and times); tickets are $55 per person.

A 4-hour bus tour to Frank Lloyd Wright sights in Oak Park ($55) includes a tour of Wright’s home and studio, a walking tour of the Frank Lloyd Wright Historic District, and a visit to Unity Temple. 

The CAC offers a variety of guided walking tours. For first-time visitors, I highly recommend two tours for an excellent introduction to the dramatic architecture of the Loop. Historic Skyscrapers covers 19th-century buildings, including the Rookery and the Marquette Building; Chicago Modern includes modern masterpieces by Mies van der Rohe and postmodern works by contemporary architects. The 2-hour tours cost $26 each.

The CAC also offers numerous neighborhood tours (see website for full list), visiting the Gold Coast, River North, Old Town, Hyde Park, and even Lincoln Park Zoo. Most cost $26 and last a couple of hours.