Flatiron Building in the context of "Madison Square Park"

Madison Square is a public square formed by the intersection of Fifth Avenue and Broadway at 23rd Street in the New York City borough of Manhattan. The square was named for Founding Father James Madison, the fourth president of the United States. The focus of the square is Madison Square Park, a 6.2-acre (2.5-hectare) public park, which is bounded on the east by Madison Avenue (which starts at the park's southeast corner at 23rd Street); on the south by 23rd Street; on the north by 26th Street; and on the west by Fifth Avenue and Broadway as they cross.

The park and the square are at the northern (uptown) end of the Flatiron District neighborhood of Manhattan. The neighborhood to the north and west of the park is NoMad ("NOrth of MADison Square Park") and to the north and east is Rose Hill.

Midtown South is a macro-neighborhood of the borough of Manhattan in New York City, generally characterized as constituting the southern portion of Midtown Manhattan. Midtown Manhattan hosts over 700,000 daily employees as a busy hub for workers, residents, and tourists. The Empire State Building, the Flatiron Building, Pennsylvania Station, Madison Square Garden, the Macy's Herald Square flagship store, Koreatown, and NYU Langone Medical Center are all located in Midtown South.

The Flatiron District is a neighborhood in the borough of Manhattan of New York City, named after the Flatiron Building at 23rd Street, Broadway and Fifth Avenue. Generally, the Flatiron District is bounded by 14th Street, Union Square and Greenwich Village to the south; the Avenue of the Americas (Sixth Avenue) and Chelsea to the west; 23rd Street and Madison Square (or NoMad) to the north; and Park Avenue South and Gramercy Park to the east.

Broadway cuts through the middle of the district, and Madison Avenue begins at 23rd Street and runs north. At the north (uptown) end of the district is Madison Square Park, which was completely renovated in 2001. The Flatiron District encompasses within its boundaries the Ladies' Mile Historic District and the birthplace of Theodore Roosevelt, a National Historic Site. The Flatiron District was also the birthplace of Silicon Alley, a metonym for New York's high technology sector, which has since spread beyond the area.

The earliest stage of skyscraper design encompasses buildings built between 1884 and 1945, predominantly in the American cities of New York and Chicago. Cities in the United States were traditionally made up of low-rise buildings, but significant economic growth after the American Civil War and increasingly intensive use of urban land encouraged the development of taller buildings beginning in the 1870s. Technological improvements enabled the construction of fireproofed iron-framed structures with deep foundations, equipped with new inventions such as the elevator and electric lighting. These made it both technically and commercially viable to build a new class of taller buildings, the first of which, Chicago's 138-foot (42 m) tall Home Insurance Building, opened in 1885. Their numbers grew rapidly, and by 1888 they were being labelled "skyscrapers".

Chicago initially led the way in skyscraper design, with many constructed in the center of its financial district during the late 1880s and early 1890s. Sometimes termed the products of the Chicago school of architecture, these skyscrapers attempted to balance aesthetic concerns with practical commercial design, producing large, square palazzo-styled buildings hosting shops and restaurants on the ground level and containing rentable offices on the upper floors. In contrast, New York's skyscrapers were frequently narrower towers which, more eclectic in style, were often criticized for their lack of elegance. In 1892, Chicago banned the construction of new skyscrapers taller than 150 feet (46 m), leaving the development of taller buildings to New York.

23rd Street is a broad thoroughfare in the New York City borough of Manhattan, one of the major two-way, east-west streets in the borough's grid. As with Manhattan's other "crosstown" streets, it is divided into its east and west sections at Fifth Avenue. The street runs from Avenue C and FDR Drive in the east to Eleventh Avenue in the west.

23rd Street was created under the Commissioners' Plan of 1811. The street hosts several famous hotels, including the Fifth Avenue Hotel and Hotel Chelsea, as well as many theaters. Several skyscrapers are located on 23rd Street, including the Flatiron Building, the Metropolitan Life Insurance Company Tower, and One Madison.

Daniel Hudson Burnham FAIA (September 4, 1846 – June 1, 1912) was an American architect and urban designer. A proponent of the Beaux-Arts movement, he may have been "the most successful power broker the American architectural profession has ever produced."

A successful Chicago architect, he was selected as Director of Works for the 1892–93 World's Columbian Exposition, colloquially referred to as "The White City". He had prominent roles in the creation of master plans for the development of a number of cities, including the Plan of Chicago, and plans for Manila, Baguio and downtown Washington, D.C. He also designed several famous buildings, including a number of notable skyscrapers in Chicago, the Flatiron Building of triangular shape in New York City, Washington Union Station in Washington D.C., London's Selfridges department store, and San Francisco's Merchants Exchange.