The Michigan Avenue Bridge is a bascule bridge that carries Michigan Avenue across the Chicago River, the boundary between the Loop and Near North Side community areas, in downtown Chicago. It lies at the foot of the Magnificent Mile, between the Wrigley Building and Tribune Tower to the north and the London Guarantee Building and 333 North Michigan across Wacker Drive to the south, and it is part of the Michigan–Wacker Historic District. The bridge was built from 1917–1920 as two parallel bridges that operate independently of one another. It was designed by architect Edward H. Bennett, and is an early example of a fixed trunnion bascule bridge, which later became widely known as a "Chicago style bascule". In spring and autumn the bridge is raised twice weekly to allow sailboats to pass between Lake Michigan and inland boat yards where they are stored for the winter. The bridge is seen in the 1996 film Chain Reaction.

The Wrigley Building is a skyscraper located directly across Michigan Avenue from the Tribune Tower on the Magnificent Mile. It was built to house the corporate headquarters of the Wrigley Company. The building was designed by the architectural firm of Graham, Anderson, Probst & White using the shape of the Giralda tower of Seville's Cathedral combined with French Renaissance details. The 425-foot (130 m) south tower was completed in April 1921 and the north tower in May 1924. Walkways between the towers were added at the ground level and the third floor. At night, the building is brightly lit with floodlights. The Wrigley Building was Chicago’s first air-conditioned office building. If one walks through the center doors, they will find themselves in a secluded park area overlooking the Chicago River.

The Tribune Tower was completed in 1925. Today it houses the city's major daily newspaper, called Chicago Tribune. This Neo-Gothic skyscraper remains a remarkable architectural monument. The building's highlights, besides architecture and design, are the many famous stones incorporated in the wall, like rock fragments from the Alamo, the Colosseum and the Chinese Wall.

The Museum of Contemporary Art opened in 1967. It claims to be one of the largest facilities in the United States devoted to the art. The focus of the museum's exhibitions is the art created since 1945. The main aim is to document contemporary visual culture through painting, sculpture, photography, video, film, and performance. The museum also features a gift store, a bookstore, a restaurant, a 300-seat theater, and a terraced sculpture garden with a great view of Lake Michigan.

The Water Tower was first built in 1869. It is one of the few constructions that survived the Great Chicago Fire in 1871. Today, the tower is considered a monument to that event. With its smaller Gothic style towers, the Water Tower looks more like a tiny European 13th century castle than a water tower. Everyone is invited to make a stop at the Visitors' Center and the City Gallery nearby.

John Hancock Center was completed in 1969. It is the sixth tallest building in the US. The Center is world known for its distinctive architecture, prestigious location and presence on Chicago's skyline. It features an observation deck that offers a spectacular view over Chicago's Downtown area.

The Palmolive Building, formerly the Playboy Building, is a 37-story Art Deco building. Built by Holabird & Root, it was completed in 1929 and was home to Colgate-Palmolive-Peet. The Palmolive Building came to be known as the Playboy Building when it was home to Playboy magazine from 1965 to 1989. During this time, the word P-L-A-Y-B-O-Y was spelled out in 9 feet (2.7 m) letters. It was designated a Chicago Landmark in 2000, and it was added to the National Register of Historic Places in 2003. Today, the building has been converted for residential use by developer Draper and Kramer. The first two floors house upscale office and retail space. High-end condos make up the rest of the building. Notable residents of the building include Vince Vaughn and Lou Piniella.

Oak Street Beach is located on North Lake Shore Drive in Chicago, Illinois, on the shore of Lake Michigan. Up until the late 1800s the Lake Shore sloped from Oak Street to the Chicago river in a much gentler fashion. However the construction of a shipping pier at the river led to a build up of sand and silt just to the north. Originally, it was under control of the Lincoln Park District, one of several districts in the city that were consolidated in 1934 to create the Chicago Park District. Through the 1960s the sand area of Oak Street covered more than twice the area it does now, and the water was as much as three feet higher than its current level. The beach was popular for residents and tourists as a summer social spot near down town.