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Chicago Then-and-Now: Behold the City’s Remarkable Urban Transformation

Chicago then vs now

Aside from its notorious politicians and its storied sports teams, what makes Chicago truly unique and such an alluring place to live is its neighborhoods, its architecture, and its lakefront.

One place where all three come together in spectacular fashion is the city’s central business district, located on the shores of beautiful Lake Michigan. For most of its history, this area was distinguished primarily by offices, retail stores, and entertainment venues. All of that changed beginning around the 1980s when residential structures were built and commercial buildings converted to create a burgeoning and livable neighborhood. Today, the area from approximately Roosevelt Road on the south, Oak Street on the north, Halsted Street on the west and the lakefront on the east, have come to encompass one of the most remarkable transformations in urban living. Though much has changed over the years, much of Chicago’s past is still reflected in the city’s 21st-century landscape.

Join us at RENTCafe as we take you on a virtual tour through Chicago’s history to see the amazing transformation of the Windy City’s streetscape over the course of the last century.

1. Chicago skyline seen from the John Hancock Center, South-Southwest View

“Big John,” as the Hancock Center is affectionately called, is one of the most iconic buildings in Chicago and when it topped out in 1968 at 1,127’, it was the second tallest building in the world. It’s called the Hancock Center rather than the Hancock building because it was originally designed to be two towers, but the additional land could not be acquired. It’s located in Streeterville – Chicago’s most quintessential neighborhood, with a storied history of its own – on the Magnificent Mile (Michigan Avenue), one of the world’s most famous streets.

Photo Credit 1973: Flickr Creative Commons by Joe+Jeanette Archie/*Photo Credit 2012: Virginia Duran Blog

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2. Navy Pier – aerial view

“Municipal Pier,” as Navy Pier was originally called, was completed in the summer of 1916 as a freighter dock with some space for public recreation. It was renamed in 1927 to honor those who served in World War I. Its history encompasses usage as a jail for draft dodgers, a World War II Naval training center, a campus for the University of Illinois – Chicago, the original location for Taste of Chicago, and finally redesigned as a mixed-use retail, dining, entertainment, and cultural venue. It’s located at the terminus of Grand Avenue in one of Chicago’s most infamous neighborhoods – Streeterville. ChicagoFest, launched in 1978 under Mayor Michael Bilandic as a “summer celebration of food and music” according to a 1986 Chicago Tribune article, was held annually at Navy Pier.

Photo Credit 1984: Wikipedia, by Louvee/*Photo Credit 2013: Tradeshows and Displays Blog

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3. Oak Street Beach, view from North Lake Shore Drive

One of the most noted beaches in the country, Oak Street Beach was formed as a result of breakwaters, built by the city at the turn of the 20th century to protect the city’s shoreline along its “Gold Coast” where so many of Chicago’s wealthy built their mansions along Lake Shore Drive. In the 1970s and 1980s, when Playboy had its headquarters overlooking the Oak Street shoreline, it was Chicago’s most popular beach where many of Playboy’s bunnies would be seen. It continues to be popular to this day, hosting numerous amateur and professional volleyball tournaments, and still a place to be seen. Part of the area’s charm is its urban residential mix: old buildings standing side by side with the modern – including the gorgeous art deco co-op building at 1242 Lake Shore Drive built in 1930, and the luxury 1300 North Lake Shore Drive and 1240 N. Lake Shore condominium towers built in 1963 and 1976, respectively.

Photo Credit 1925: Wikipedia, author unknown/*Photo Credit 2015: Google Street View

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4. Chicago skyline seen from Lake Michigan

There are few shoreline vistas as magnificent as the lakefront along downtown Chicago, but it wasn’t always so beautiful. Were it not for the intervention of Montgomery Ward, the catalog millionaire who had his office overlooking what is now Grant Park in the late 19th century, it might be an industrial and railroad wasteland today. Instead, due to his perseverance and of many others to follow, including Plan of Chicago architect Daniel Burnham, Chicago’s lakefront is one of the most spectacular urban waterfronts to be found anywhere in the world, much less in the United States.

Photo Credit 1926: Flickr Creative Commons, by Snapshots of the Past/*Photo Credit 2011: Wikimedia by Bladerunner2019

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5. Monroe Street, looking East from Wells Street

First National Bank of Chicago could trace its founding back to 1863. Over time, the bank occupied a number of buildings and locations, including its longest occupancy from 1903 to 1970 at the corner of Monroe and Dearborn. The site was located across the street from the infamous four-story gambling house known as “The Store,” operated by “King Mike” McDonald, who ran Chicago’s first crime syndicate and is said to have laid the foundation for Chicago’s political machine. The bank building was eventually razed to become the plaza of the Chase Bank building, preserving only the clock.

Photo Credit 1955: Flickr Creative Commons by Joe+Jeanette Archie/*Photo Credit 2015: Google Street View

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6. Warren Blvd. at Paulina Street

The intersections of Warren Boulevard and Paulina Streets are in the heart of one of Chicago’s hottest neighborhoods – the Near West Side – and a block from Chicago’s popular Union Park. The community has one of the richest histories in the city, being the site of the Great Chicago Fire, the original Hull House, the original Maxwell Street Market, and today home to the University of Illinois Chicago campus, the United Center, and the University of Illinois medical district. Only minutes from downtown Chicago, the neighborhood has become an attractive location for those working in the Loop.

Photo Credit 1954: Flickr Creative Commons by Joe+Jeanette Archie/*Photo Credit 2014: Google Street View

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7. Chicago skyline seen from the Wrigley Building

The Wrigley Building is located on Michigan Avenue, also known as The Magnificent Mile, across the river from one of the Chicago’s most historic landmarks – Fort Dearborn, which was one of the earliest settlements in the area. The Wrigley Building itself is also a designated historic landmark, whose architecture and white terra-cotta cladding are modeled after the Giralda tower of the cathedral in Seville. In January 1920, when excavation for the structure began, the Michigan Avenue Bridge was under construction. The 27-story 425-foot south tower was completed in 1921 and until 1924 it was the tallest building in Chicago. The north tower was completed in 1924; it was connected to the south section with walkways at street level and between the third floors. Later, in 1931, a 14th floor enclosed walkway was put in place. It still remains today as the headquarters of the Wrigley chewing gum company.

One of The Wrigley Building’s most prominent neighbors, the Carbide and Carbon building was built in 1929 to accommodate the regional headquarters of Union Carbide and Carbon Co. Featuring a polished black granite base and a tower covered in deep green terra cotta, the art deco building now houses Hard Rock Hotel Chicago.

Photo Credit 1950: Flickr Creative Commons by Joe+Jeanette Archie/*Photo Credit 2016: Wrigley Building Facebook

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8. Michigan Avenue Bridge

The Michigan Avenue Bridge, opened to traffic on May 14, 1920, is what is known as a bascule bridge, which is French for “balance scale” – a bridge that moves by use of a counterweight to balance a “leaf” through its upward swing allowing clearance for boat traffic. The idea for the bridge was conceived by Daniel Burnham, in his 1909 “Plan of Chicago”, to connect traffic across the Chicago River along what was then known as Pine Street. Considered an engineering marvel of its time, it requires only two 108-horsepower motors to open and close each of its 3,750-ton bridge leafs.

Photo Credit 1931: Chicago Public Library Blog by Municipal_Reference_Guy. Source: Chicago Board of Local Improvements/*Photo Credit 2006: Wikipedia by JeremyA

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9. The Old Colony Building, view from South Dearborn Street

Originally named as an homage to the Plymouth Colony, the Old Colony Building was completed in 1894 and at the time was the tallest building in Chicago. Located at the north edge of what was at the time the Levee District of Chicago – the city’s most infamous gambling and prostitution vice-district ruled over by a pair of Chicago’s most notorious aldermen, Hinky Dink Kenna and Bathhouse John Coughlin. Originally built as an office building, it was placed on the National Register of Historic Places in 1976 and in 2015 it was completely renovated into a 490-bed student housing complex.

Photo Credit 1964: Wikimedia, by Harold Allen-photographer/*Photo Credit 2015: Google Street View

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10. The Auditorium Building, view of the exterior from the Southeast

Possibly one of the most famous buildings in the City of Chicago, the Auditorium Building was placed on the National Register of Historic Places in 1970, and designated a National Historic Landmark in 1975 – and rightfully so. Designed by two of Chicago’s most famous architects, Louis Sullivan and his young apprentice, Frank Lloyd Wright, who designed some of the interior, the building was completed in 1889. The building is also significant for its almost perfect acoustics, designed by Sullivan’s partner, Dankmar Adler. It’s located on the campus of Roosevelt University in the South Loop.

Also visible in the background is the historic landmark’s contemporary counterpart – Roosevelt University’s Wabash Building. Located immediately next to the Auditorium building, the 32-story vertical campus was completed in 2012 and stands 469 feet tall.

Photo Credit 1963: Wikipedia, by Cervin Robinson, photographerPhoto Credit 2014: Google Street View

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Fair use and redistribution

We encourage you and freely grant you permission to reuse, host, or repost the images in this article. When doing so, we only ask that you kindly attribute the authors by linking to or this page, so that your readers can learn more about this project, the research behind it and its methodology.

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About the author

Ama Otet

Ama Otet is an online content developer and creative writer for RENTCafé. She loves all things real estate and strives to live beautifully, one green step at a time. You can connect with Ama on Twitter or via email.


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