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.

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.

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.

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.

Chicago’s Union Station has served as the city’s primary railroad hub since its completion in 1925. Designed by the renowned Chicago architect Daniel Burnham, who also designed Washington, D.C.’s Union Station, and completed by the architectural firm Graham, Anderson, Probst and White, the Beaux-Arts style building took ten years to complete at the cost of $75 million dollars (the equivalent of $1 billion dollars in 2017). Union Station is the only station in the United States that possesses what is known as a double-stub, where the station’s 24 tracks approach from two directions without continuing under or through the station. In 1991, a lengthy $32 million-dollar facility improvement restoration project was completed, and the station was designated a Chicago Landmark in 2002. Chicago Union Station is Amtrak’s fourth busiest station, serving over three million customers per year.