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Chicago’s architecture is world famous. Luckily, the Chicago Architecture Foundation offers first-rate guided tours to help visitors understand what makes this city’s skyline so special. 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 CAF 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 CAF’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 (10am–5:30pm Mon–Thurs [7:30pm Thurs], from 9:30am–7:30pm, 9am–5:30pm Sat and 9am–7:30pm Sun); the cost is $38 per person. 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 Friday and Saturday year-round, with additional tours on Wednesdays and Sundays from April through October; tickets are $45 per person.

A 4-hour bus tour of Frank Lloyd Wright sights in Oak Park ($45) is available on the first Saturday of the month from May to October. The tour includes walks through three neighborhoods and commentary on more than 25 houses—but does not take visitors inside Wright’s home and studio.

The CAF 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 Downtown: Rise of the Skyscraper (daily 10am) covers buildings built between 1880 and 1940, including the Rookery and the Chicago Board of Trade; Modern Skyscrapers (daily 1pm) includes modern masterpieces by Mies van der Rohe and postmodern works by contemporary architects. The 2-hour tours cost $17 each.

The CAF also offers more than 50 neighborhood tours (see website for full list), visiting the Gold Coast, River North, Grant Park, Old Town, the Jackson Boulevard Historic District, and even Lincoln Park Zoo. Most cost $10 and last a couple of hours.