The best resource for anyone interested in urban design is the Chicago Architecture Foundation Shop and Tour Center (224 S. Michigan Ave. +1 312 922 8687. Fee for tours. Reservations required for bus tours and river cruises). The foundation’s docents lead visitors on downtown bus and walking tours, and also on cruises that glide beneath the Chicago River’s many bridges for a unique look at landmark buildings.Architectural tastes vary, but there are several can’t-miss structures worth seeing on your own or by tour. Shoppers can mask their passion for purchase behind a veneer of historical curiosity at two magnificent turn-of-the-century department stores: Carson Pirie Scott (1 S. State St. +1 312 641 7000), an 1899 Louis Sullivan masterpiece with cast-iron floral ornaments, and Marshall Field’s (835 N. Michigan Ave. +1 312 335 7700), with its big atrium and iron fountain in the midst of 73 acres [29.5 hectares] of floor space. Both stores have been renovated extensively and feature specialty shops for the most au courant tastes.
A few blocks away stands the 1930 art deco Chicago Board of Trade (141 W. Jackson Blvd. +1 312 435 3590. Mon.-Fri.), housing the oldest and largest futures exchanges. Traders jam together in a frenzied crush of buying and selling that may look like a deranged rugby match from the gallery. In fact, fortunes are being made and lost with the wave of a frantic hand.
North of the Michigan Avenue Bridge rise two 1920s gems, the Wrigley Building (400 N. Michigan Ave.), a white sugar confection of terra-cotta, and the 1922 Tribune Tower (435 N. Michigan Ave.), a mammoth Gothic structure with flying buttresses and imbedded stones stolen from the Parthenon and the Egyptian Pyramids by the newspaper’s reporters. Ludwig Mies van der Rohe brought Chicago into the modern era with designs such as the Federal Center (219 S. Dearborn St.), wher e solid slabs of Bauhaus are offset by Alexander Calder’s curvaceous "Flamingo" sculpture.
Calder’s sculpture is only one of many monumental outdoor artworks that decorate the city. The artists’ roster is a who’s who of 20th-century greats: There are Picasso’s untitled 1967 50-foot-tall [15.2-meter-tall] sculpture at Richard J. Daley Civic Center Plaza (50 W. Washington Blvd.), a popular site for public demonstrations; Marc Chagall’s huge mosaic, "The Four Seasons," at the First National Plaza (Dearborn and Monroe Sts.); Claes Oldenburg’s amusing 100-foot [30.5-meter] "Batcolumn" at the Harold Washington SSA Building Plaza (600 W. Madison St.); and many others, described in a guide available at the Visitor Centers.
A few other downtown attractions shouldn’t be missed. The Chicago Athenaeum (6 N. Michigan Ave. +1 312 251 0175. Closed Mon.; Adm. fee) features fascinating displays on architecture and industrial design from radios to ice-cream scoops; and the spacious new Museum of Contemporary Art (220 E. Chicago Ave. +1 312 280 2660. Closed Mon.; Adm. fee) offers airy exhibit areas for modern sculpture and paintings.
In the evening, Chicago offers the unquenchable variety you would expect in a cosmopolitan city, from the Chicago Symphony (220 S. Michigan Ave. +1 312 294 3000. Adm. fee) to the comedy club Second City (1616 N. Wells St. +1 312 337 3992. Adm. fee) to the world-champion Chicago Bulls (United Center, 1901 W. Madison St. +1 312 455 4500. Adm. fee) during basketball season. What Chicago has that no other city can match—well, besides Michael Jordan—is a lineup of blues clubs that define the idiom. A good place to start is Buddy Guy’s Legends (754 S. Wabash Ave. +1 312 427 1190. Adm. fee), where you may get lucky and find the guitar giant himself jamming with his old harmonica-mate, Junior Wells.
Best to get back in the car for visits to the city’s fringes. On the South Side you can tour the Gothic Revival buildings of the University of Chicago (1212 E. 59th St. +1 773 702 8374), including the Rockefeller Memorial Chapel (5850 S. Woodlawn Ave. +1 773 702 9292. Call for carillon concert schedule), a structure designed by Bertram Goodhue. Also on campus is the Robie House (5757 S. Woodlawn Ave +1 773 834 1361. Adm. fee), one of Frank Lloyd Wright’s Prairie School designs.