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Whether you’re a shopper or not, this store-lined strip warrants a visit if only to get a feel for the commercial pulse that seems to keep Chicago humming.

Skidmore, Owings & Merrill designed this 1970 landmark using the signature X’s on the facade as cross-braces to help the 1,100-ft (335-m) building withstand the winds coming off Lake Michigan. An alternative to soaking up the view from the 94th-floor observatory is drinking it in from the Signature Room restaurant and lounge on the floors directly above. Many say you get a better view from here than from the South Side’s Sears Tower – and the lines are usually shorter too.

This massive two-square-block edifice houses Chicago’s premier interior design trade showrooms. When completed in 1930, the four million-sq-ft (390,000-sq-m) building was the largest in the world. Today, it is second only to the Pentagon in size, and is still the world’s largest commercial building. A 90-minute guided tour includes a visit to several showrooms.

One of the country’s largest collections of international contemporary art, the MCA displays over 6,000 objects, from painting and sculpture to photography and video installations. Trendy Spago chef Wolfgang Puck runs the airy café, which draws both museum-goers and Mag Mile shoppers alike. In summer, the terraced sculpture garden enhances the MCA experience, while the front lawn often plays host to displays of performance art.

Said to be the most concentrated art hub in the US outside of Manhattan, this district is jammed with great galleries. Most are to be found in the handsome, 19th-century, converted brick warehouses found along either side of the El brown line. Huron and Superior Streets are particularly worth a visit.

Chicago boasts many upscale neighborhoods, but none more historic and prestigious than the Gold Coast. Railroad, retail, and lumber tycoons built this elegant district in the decades following the Great Fire of 1871 (see 1871: Great Chicago Fire), and its leafy streets are lined with 19th-century mansions interspersed with early 20th-century apartment buildings. There are no less than 300 designated historic landmarks in the Astor Street District alone, including buildings by Stanford White (such as 20 E. Burton Place), and Charnley House, designed by Louis Sullivan (assisted at the time by Frank Lloyd Wright). (1365 N. Astor Street).

When the Great Fire of 1871 swept north, only the 1869 Water Tower and Pumping Station escaped ruin. Built by William W. Botington, the castellated Gothic-Revival Water Tower, modeled after a medieval castle, was once called a “monstrosity” by critic Oscar Wilde. It now houses the City Gallery (specializing in photography), and the fountain and chairs outside make it a focal point for downtown street life. The Water Pumping station across the street still functions, and also houses a visitor center and the Lookingglass Theater, co-founded by Friends star David Schwimmer.

Topped by flying buttresses, this Gothic-style building was completed in 1925. Its faux historic design had won a competition organized by Colonel Robert McCormick, publisher of the Chicago Tribune , the newspaper whose offices still occupy the building. Look closely at the facade, which is embedded with over 120 stones collected by correspondents from famed sights. There’s a rock hailing from each of the 50 states, as well as fragments from international monuments such as Greece’s Parthenon, India’s Taj Mahal, and The Great Wall of China.

The first Fourth Presbyterian church, dedicated in 1871, celebrated its first sermon just hours before it was incinerated in the Great Fire. Rebuilt in 1914 when Magnificent Mile was the little-used Pine Street, today’s church offers often peaceful respite from the now highly commercial boulevard. Designed by Ralph Adams Cram, one of the architects behind New York’s Cathedral of St. John the Divine, it’s not surprising that this church boasts a cathedral-like interior, with an impressive stained-glass west window. A tranquil courtyard is often the place for classical concerts in summer.

When candy-manufacturer Milton Hershey visited the city of Chicago in 1893, he purchased the equipment that he would use to revolutionize the chocolate industry. With mass production he was able to lower the cost of manufacturing milk chocolate, once a luxury item, making it affordable to all. Today, the Hershey Foods Corporation is the largest North American producer of chocolate and non-chocolate confectionary. Hershey’s Chicago, a new themed store on Magnificent Mile, stocks all the well-known brands such as Hershey’s, Reese’s, and Kit Kat, as well as the latest products and goods unique to the Chicago store. Sugar-free versions of the most popular products are also available. A hit with children is the store’s interactive “bake shoppe” where visitors can customize cookies, cupcakes, and brownies.