Buckingham Fountain is a Chicago landmark in Grant Park which was dedicated in 1927. The fountain is considered to be Chicago's front door, since it resides in Grant Park, the city's front yard. The fountain, located at Columbus Drive and Congress Parkway, was designed with sculptures by Jacques Lambert. The fountain itself represents Lake Michigan, while each sea horse symbolizes a state bordering the lake. The statues were created by the French sculptor Marcel F. Loyau. The design of the fountain was based on the Bassin de Latome and modeled after Latona Fountain at Versailles. The fountain runs from 8:00 a.m. to 11:00 p.m. every day from mid-April to mid-October. During a water display that runs for 20 minutes every hour on the hour, the center jet shoots up to 150 feet (46 m) in the air. At dusk, a light and music show coincides with the water display. The last show of the night begins at 10:00 p.m. Each display lasts for 20 minutes.

The Auditorium Building was originally built in 1889 as Chicago's Opera House. Today, it combines a hotel, office space and a spectacular theater. The building features Eclectic Romanesque Revival architectural style. Its main highlights are the proscenium arch over the theater stage painted with 45 life-size classical figures, and the mosaics inside the building which are estimated to include 50 million pieces of marble.

Fine Arts Building was constructed in 1884. It is one of the few remaining buildings in Chicago designed specifically for working artists. The bronze cast elevator doors and ornate clocks are among the building's original features. This historic building houses two theaters, several offices, some amazing shops and music studios.

The Harold Washington Library Center is the central library for the Chicago Public Library System. It opened to the public October 7, 1991. The exterior evokes the design of the Rookery, Auditorium and the Monadnock buildings, among others. The bottom portion is made of large granite blocks. Red brick makes up the majority of the exterior. These two portions draw on the Beaux-Art style. The pediments and most of the west side, facing Plymouth Court, are glass, steel and aluminum with ornamentation harkening to the Mannerist style. In 1993, the roof was ornamented with seven large, ornate, bronze acroteria designed by Raymond Kaskey. The acroterium on the State Street side depicts an owl, the Greek symbol of knowledge. The acroteria on the Congress Parkway and on the Van Buren sides contain seed pods, which represent the natural bounty of the Midwest. The acroteria angularia each contain an owl perched in foliage.

The Fisher Building is 20-story, 275-foot-tall neo-Gothic landmark building located at 343 South Dearborn Street in the Chicago Loop community area of Chicago. It was designated a Chicago Landmark on June 7, 1978. At the time of its completion, the building was one of two buildings in the city that was 18 stories tall, the other being the Masonic Building. To this day, the Fisher Building is the oldest 18 story building in Chicago that has not been demolished. The Fisher Building features terra-cotta carvings of various aquatic creatures including fish and crabs. In addition, there are eagles, dragons and mythical creatures depicted on the facade as well. The building was added to the National Register of Historic Places on March 16, 1976.

The Marquette Building, completed in 1895, is a Chicago, Illinois landmark that was built by the George A. Fuller Company and designed by architects Holabird & Roche. The building was one of the early steel frame skyscrapers of its day, and is considered one of the best examples of the Chicago School of architecture. The architects, Holabird & Roche, used trademark long horizontal bay "Chicago windows" on the Marquette Building. These are large panes of glass flanked by narrow sash windows. The grid-like window frames and spandrels are facilitated by the steel structure which enables non-load-bearing masonry walls. The ensemble of mosaics, sculptures, and bronze of the Marquette Building entry and interior honors Jacques Marquette’s 1674-5 expedition. The mosaics are by Louis Comfort Tiffany and his chief designer and art director, Jacob Adolph Holzer; they contain panels of lustered Tiffany glass, mother-of-pearl, and semi-precious stones.

The Rookery Building is a historic landmark located in the Loop community area of Chicago in Cook County, Illinois, United States. Completed by John Wellborn Root and Daniel Burnham of Burnham and Root in 1888, it is considered one of their masterpiece buildings. It measures 181 feet (55 m), is twelve stories tall and is considered the oldest standing high-rise in Chicago. It has a unique style with exterior load-bearing walls and an interior steel frame. The building was designated a Chicago Landmark on July 5, 1972. The name Rookery comes from the previous building on the property, which became home to many birds, especially pigeons. The red marble, terra cotta and brick facade of the building is a combination of Roman Revival and Queen Anne styles that embraced Richardsonian Romanesque architecture. The building, which is a combination of iron framing and masonry bearing walls, marked a transition from masonry load-bearing structures to steel skeleton load-bearing structures.

Willis Tower, formerly named Sears Tower, is a 108-story 1,451 feet (442 m) skyscraper in Chicago, Illinois. At the time of its completion in 1973, it was the tallest building in the world, surpassing the World Trade Center towers in New York. Currently, Willis Tower is the tallest building in the United States and the fifth-tallest freestanding structure in the world as well as the fifth tallest building in the world to the roof. Skydeck Chicago at Willis Tower opened as The Sears Tower Skydeck observation deck on June 22, 1974. It is located on the 103rd floor of the tower. It is 1,353 feet (412 m) above ground and is one of the most famous tourist attractions in Chicago. Tourists can experience how the building sways on a windy day. They can see far over the plains of Illinois and across Lake Michigan to Indiana, Michigan and Wisconsin on a clear day. It takes about 60 seconds to soar to the top in either of two special, Schindler Group elevators.

Union Station, built in 1925 is a historical landmark in Chicago, the last remaining of Chicago's great turn-of-the-century train depots. The main highlight of the Union Station is the Great Hall. It is a 20,000 foot classic Beaux Arts style room which boasts 18 soaring Corinthian columns, terracotta walls, a pink Tennessee marble floor and a spectacular five-story, barrel-vaulted, atrium ceiling, that crowns the room.

Old St. Patrick's Church is one of the Chicago's most famous religious buildings. It was built in 1854. The church features Romanesque architectural style. It is one of the few buildings that survived the Great Chicago Fire of 1871, being today the oldest public building in the City of Chicago. The church is characterized by a spectacular interior, with amazing stained glass windows, marble ceiling and unique paintings.

One of the world's most beautiful constructions, Civic Opera House, is located in the heart of Downtown Chicago, in the famous Loop District. The construction of the building is characterized as a hybrid of Art Deco and Art Nouveau architectural styles. This venue houses the world-known Lyric Opera of Chicago.

Chicago City Hall is the official seat of government of the City of Chicago in Illinois. Situated on a city block bounded by Randolph, LaSalle, Washington, and Clark streets, the 11-story structure was designed by the architectural firm Holabird & Roche in the classical revival style. The building was officially dedicated on February 27, 1911. Chicago City Hall's entrance features four relief panels sculpted in granite by John Flanagan. Each of the panels represents one of four principal concerns of city government: playgrounds, schools, parks, and water supply. As visitors enter the building, they are greeted with elaborate marble stairways and bronze tablets honoring the past city halls of Chicago from 1837 to the present. In 2001, the roof gardens were completed serving as a test for the impact green roofs would have on the heat island effect in urban areas, rainwater runoff, and the effectiveness of differing types of green roofs and plant species for Chicago's climate.

The Chicago Theatre, originally known as the Balaban and Katz Chicago Theatre, is a landmark theater located on North State Street in the Loop area of Chicago, Illinois. When it opened on October 26, 1921, the 3,880 seat theater was promoted as the "Wonder Theatre of the World". Now the Chicago Theatre is a performing arts venue for stage plays, magic shows, comedy, speeches, and popular music concerts. The building was added to the National Register of Historic Places on June 6, 1979, and it was listed as a Chicago Landmark on January 28, 1983. The iconic Chicago Theatre marquee, "as an unofficial emblem of the city", appears in film, television, artwork, and photography. The structure is seven stories tall and fills nearly one half of a city block. The interior shows French Baroque influence from the Second French Empire. The grand lobby, five stories high and surrounded by gallery promenades at the mezzanine and balcony levels, is influenced by the Royal Chapel at Versailles.

The Aqua Tower is located on the 200 block of North Columbus Drive, and is surrounded by high-rises. Aqua is an 86-story mixed-use residential skyscraper in the Lakeshore East development in downtown Chicago. Designed by a team led by Jeanne Gang, the building is the tallest in the world, at 859 ft, to have a woman as lead architect. The Aqua was named the Emporis Skyscraper Award 2009 skyscraper of the year and was shortlisted in 2010 for the biannual International Highrise Award. To capture views of nearby landmarks for Aqua's residents, Gang stretched its balconies outward by as much as 12 feet. The result is a building composed of irregularly shaped concrete floor slabs which lend the facade an undulating, sculptural quality. The green roof on top of the tower base will be the largest in Chicago.