Michigan Avenue is a major north-south street in Chicago which runs at 100 east (except for one private block that runs at 125 east) south of the Chicago River and at 132 East north of the river from 12628 south to 950 north in the Chicago street address system. As the home of the Chicago Water Tower, the Art Institute of Chicago, Millennium Park, and the Magnificent Mile, it is a street well known to Chicago natives as well as tourists to the city. Michigan Avenue also is the main commercial street of Streeterville. It includes all of the Michigan Boulevard Historic District and most of the Michigan–Wacker Historic District.

History currently borders Grant Park. The name came from Lake Michigan, which until 1871 was immediately east of Michigan Avenue. The street at that time ran north to the Chicago river and south to the city limits. Originally, Michigan Avenue was primarily residential, and by the 1860s, large homes and expensive row houses dominated Michigan Avenue. In the Great Fire of 1871, all buildings on Michigan avenue from Congress Street north to the river were destroyed. Immediately after the fire, the character of Michigan remained residential, but the street no longer was directly on the lake shore, as after the Fire, wreckage from the burnt district was used to fill in the inner harbor of Chicago, beginning the landfills that by the 1920s had moved the lake shore more than a quarter-mile east of its original shoreline. Beginning in the 1880s, the expansion of the central business district replaced houses on Michigan avenue so that today, Michigan's character is primarily commercial north of 35th Street.

The first city showcase on Michigan Avenue was the Exposition Building, which was built on the current site of the Art Institute, the east side of Michigan at Adams, in 1874. By the 1890s, an imposing wall of buildings was constructed on the west side of Michigan Avenue downtown, including the Auditorium Building and the main branch of the Chicago Public Library (now the Chicago Cultural Center). As the east side of Michigan Avenue downtown was developed as a park, the wall of buildings lining the west side of Michigan Avenue across from the park became the nucleus of the city's skyline.

In 1924, the first traffic lights in Chicago were installed on Michigan Avenue after John D. Hertz fronted the city $34,000 for the purchase, installation, and maintenance.

As Michigan had no bridge at first, it ended at the Chicago River. What is now Michigan Avenue north of the river was originally named Pine Street, after scattered pine trees originally found in its vicinity. Daniel Burnham proposed connecting Michigan and Pine in his 1909 Plan of Chicago, and in 1917, work on the bridge began. When the Michigan Avenue bridge was completed, Pine Street was renamed Michigan Avenue. At its north end it merges into Lake Shore Drive near the Drake Hotel.

Today, the area north of the Chicago River is referred to as the Magnificent Mile, or sometimes simply the Mag Mile. It contains a mixture of upscale department stores, restaurants, high-end retailers, office buildings and hotels, and caters primarily to tourists and the affluent. The area also has a high concentration of the city's major media firms, and advertising agencies, including the Chicago Tribune newspaper. The major hotels present on the street are The Four Seasons, Ritz-Carlton, The Peninsula, Intercontinental, Westin, Hard Rock Hotel, and The Drake.

It is the home of Chicago's famous Water Tower landmark, Water Tower Park with its historic clock, as well as the eight-level Water Tower Place shopping center which grew up next door to, and overshadowed, the comparatively diminutive landmark. The shopping center is anchored by Macy's North Michigan store. Lord and Taylor closed their location at the Water Tower Place in March of 2007. Within a two block radius of Macy's, there is also the Chicago flagship Saks Fifth Avenue, Barneys New York, Neiman Marcus, and Bloomingdale's locations. North of the shopping center can be found the famous John Hancock Center, the art deco Palmolive Building (also known as the Playboy Building) and the lavish Drake Hotel.

The Magnificent Mile is also the home of luxury hotels around the historic Chicago Water Tower Square. Across the historic Water Tower Square lies the Park Tower / Park Hyatt Hotel, one of the most successful luxury hotel/residential buildings in Chicago. The entire mile is noted for its spectacular Christmas displays. At the northern edge of this district can be found the exclusive One Magnificent Mile building; Chicago Landmark East Lake Shore Drive District, an extremely expensive and exclusive one-block area of real estate running east from North Michigan Ave. and facing directly onto to Lake Michigan; and the on-ramp to northbound Lake Shore Drive.

There are also numerous high-end salons on Oak Street. Unlike Michigan Avenue and Water Tower Place, which feature upscale chain stores and large department stores, Oak Street is known for its small exquisite boutiques. A few boutiques are so exclusive that they will only open doors for select patrons or prefer prior appointments.

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