Located in the Loop District of Chicago, the Monadnock building, originally known as the Monadnock Block, is a skyscraper whose construction began in 1891. The oldest section of the building, the north half, was designed by the architectural firm Burnham and Root and was the tallest load-bearing brick building in the world. The southern half of the building was designed by Holabird and Roche in 1893 and features more ornamental design elements. At the time of its completion in 1893, the Monadnock Building was the largest office building in the world.

Built in 1896, the Fisher Building stands as a reminder of the early influence of the Chicago School of Architecture and the subsequent emergence of the skyscraper. When completed, the Fisher Building was one of the tallest buildings in the world. Commissioned by paper tycoon Lucius Fisher, president of the Union Bag and Paper, it is located just north of the historic Printer's Row in Chicago. A 2001 renovation and restoration of the Fisher Building ostensibly converted it from an industrial space to that of residential use.

The Chicago Board of Trade Building is a skyscraper located in Chicago, Illinois, United States. It stands powerfully as a gateway to the city's financial district, at the foot of the LaSalle Street canyon, in the Loop community area in Cook County. Originally built for the Chicago Board of Trade (CBOT) in 1930, it is now the primary trading venue for the derivatives exchange, the CME Group, formed in 2007 by the merger of the CBOT and the Chicago Mercantile Exchange. This 45-story edifice was designed by the distinguished architectural firm of Holabird & Root. Designed in “Art Deco” style, clad in gray Indiana limestone, capped with a pyramid-shaped roof, this 605 ft (184 m) tall skyscraper was the tallest building in Chicago until 1965. It serves as the southern border for the skyscrapers hugging LaSalle Street and is taller than surrounding structures for several blocks. This Art Deco building incorporates sculptural work by Alvin Meyer and is capped by a 31 foot (9.5 m) tall aluminum statue of the Roman goddess “Ceres” - Goddess of Grain and Harvest, in reference to the exchange's heritage as a commodity market. Ceres is faceless because its sculptor, John H. Storrs (one of the leading 1920s sculptors) , believed that the forty-five story building would be sufficiently taller than any other nearby structure, and as a result no one would be able to see the sculpture's face anyway.

Built in 1895 by the George A. Fuller Company, this Chicago landmark was one of the first steel-framed skyscrapers in the city. The building was named in honor of the French missionary Jacques Marquette, who with Louis Jolliet in 1674, became the first European to explorer and map the lands around Lake Michigan. The building was served as corporate headquarters to numerous railroad companies and other businesses over the years. During the mid-20th century, some of the historic buildings throughout the Loop such as Louis Sullivan's Stock Exchange were demolished in favor of new construction. The Marquette Building, like so many of the other historic buildings throughout the Loop, was saved due to the efforts of preservationists and community members who partnered with local government and business leaders. Since 1975, the building has been owned by the John D. and Catherine T. MacArthur Foundation, a leading supporter of education that is also working with the Landmarks Preservation Council of Illinois to restore and share the history of this building. The Foundation operates an interactive exhibit on the building's first floor that is open to the public, as well as virtual exhibits that are available by clicking on the link below.

The Federal Reserve Bank of Chicago, also known as the Chicago Fed, began operations on November 16, 1914. At the time, James B. McDougal served as the president of the Chicago Fed and oversaw the bank's 41 employees. However, the bank soon outgrew its space in the Rector Building at Clark and Monroe. The Chicago Fed's Board of Directors commissioned the architectural firm of Graham, Anderson, Probst and White to construct the current building at South LaSalle Street. Completed in 1922, the Chicago Fed has remained at this building since. The Board of Governors in Washington, DC and the Federal Reserve Bank of Chicago serve together as the nation’s central bank.

Built in 1914, the seventeen-story Fort Dearborn Hotel arrived when Chicago's population had reached two million. The immense population and economic boom resulted in many business travelers passing through, and the Fort Dearborn Hotel catered to those clients.

At the time of its completion in 1891, Chicago’s Manhattan Building was one of the most innovative buildings of the era. Designed by William Le Baron Jenney, he sought to push the limits of building height during a time when the traditional practices of architecture were being questioned and experiments with new designs and ideas began taking shape. At that time, constructing a building at such a height of 16-stories was generally thought to be unsafe. To remedy that concern, Jenney designed the Manhattan Building to feature horizontal sections and setbacks which creates an allusion of a shorter building. Today, the Manhattan Building is the third-oldest skyscraper in Chicago and is the earliest surviving skyscraper relying on an entirely steel skeletal support structure.

The Civic Opera House, also referred to as the Lyric Opera House, opened fully in November of 1929. The structure includes a main tower and two wings; a forty-five-story office tower connected to twenty-two story wings on both sides. The building includes the 3,563-seat, Ardis Krainik auditorium, which is the second-largest opera space in North America behind the Metropolitan Opera House. The hall operates as the permanent home of the Lyric Opera of Chicago.

Completed in 1911, Chicago City Hall was designed by the architectural firm Holabird & Roche. The building is home to the offices of the mayor, the city treasurer of Chicago, the City Clerk, some of the city’s departments, the wards of the various aldermen of Chicago, and the chambers of the Chicago City Council. It reaches 11 stories and was built in the classical revival style. The classical revival style, or neoclassicism, refers to Western movements in visual arts, literature, theatre, music, and architecture at various points throughout history that were inspired by stylistic elements of Ancient Greek and Ancient Roman art.

Designed for the Central Safety Deposit Company by John Wellborn Root and Daniel Burnham, of the architectural firm Burnham & Root, and completed in 1888, the Rookery is one of Chicago’s most elegant and revered buildings. At the time of its completion, the Rookery was one of the tallest buildings in the world. Originally standing at eleven stories, the building is considered a precursor of the modern high-rise due to its innovative construction methods that combined steel, iron, and masonry. By 1905, Edward C. Waller, the building’s manager, sought to update and modernize the building’s interior and hired Frank Lloyd Wright. Considered one of Wright’s most luxurious interiors, he transformed the interior of the Rookery into a bright marbled and gold light court. While other alternations occurred to the building since Wright’s interior update, the architectural integrity of the building remains today thanks to a major renovation during the late 1980s and early 1990s. The Rookery was added to the National Register of Historic Places in 1970, designated as a Chicago Landmark in 1972, and designated as a National Historic Landmark on May 15, 1975.

The Harold Washington Library Center (HWLC) is the main branch of the Chicago Public Library system. In 1987, the branch and its location were strongly advocated for by then Chicago Mayor Harold Washington. Mayor Washington wished to solve two issues; revitalizing what had become a seedy district in downtown Chicago and making a main central library when none existed at the time. Mayor Washington authorized a design contest for the library, but died before the contest was over. The city subsequently picked a design by architect Thomas Beeby (of Hammond, Beeby, and Babka) as the contest winner and the new library, named for Mayor Washington, opened its doors on October 7th, 1991.