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The Aon Center (200 East Randolph Street, formerly Amoco Building) is a modern supertall skyscraper in the Chicago Loop, Chicago, Illinois, United States, designed by architect firms Edward Durell Stone and The Perkins and Will partnership, and completed in 1974 as the Standard Oil Building. With 83 floors and a height of 1,136 feet (346 m), it is the fourth-tallest building in Chicago, surpassed in height by Willis Tower, Trump International Hotel and Tower, and St Regis Chicago. The building is managed by Jones Lang LaSalle, which is also headquartered in the building. Aon Center formerly housed the world headquarters of Aon and Amoco. Aon still maintains headquarters of its US operations there. The building is also the co-headquarters of Kraft Heinz.

The Joan W. and Irving B. Harris Theater for Music and Dance (also known as the Harris Theater for Music and Dance, the Harris & Harris Theater or, most commonly, the Harris Theater) is a 1,499-seat theater for the performing arts located along the northern edge of Millennium Park on Randolph Street in the Loop community area of Chicago in Cook County, Illinois, US. The theater, which is largely underground due to Grant Park-related height restrictions, was named for its primary benefactors, Joan and Irving Harris. It serves as the park's indoor performing venue, a complement to Jay Pritzker Pavilion, which hosts the park's outdoor performances. Constructed in 2002–2003, it provides a venue for small and medium-sized music and dance groups, which had previously been without a permanent home and were underserved by the city's performing venue options. Among the regularly featured local groups are Joffrey Ballet, Hubbard Street Dance Chicago, and Chicago Opera Theater. It provides subsidized rental, technical expertise, and marketing support for the companies using it, and turned a profit in its fourth fiscal year. The Harris Theater has hosted notable national and international performers, such as the New York City Ballet's first visit to Chicago in over 25 years (in 2006). The theater began offering subscription series of traveling performers in its 2008–2009 fifth anniversary season. Performances through this series have included the San Francisco Ballet, Mikhail Baryshnikov, and Stephen Sondheim. The theater has been credited as contributing to the performing arts renaissance in Chicago and has been favorably reviewed for its acoustics, sightlines, proscenium and for providing a home base for numerous performing organizations. Although it is seen as a high caliber venue for its music audiences, the theater is regarded as less than ideal for jazz groups because it is more expensive and larger than most places where jazz is performed. The design has been criticized for traffic flow problems, with an elevator bottleneck. However, the theater's prominent location and its underground design to preserve Millennium Park have been praised. Although there were complaints about high priced events in its early years, discounted ticket programs were introduced in the 2009–10 season.

The Consulate General of Canada in Chicago is a Government of Canada diplomatic mission responsible for Canadian interests in the states of Illinois, Missouri, Wisconsin, northwestern Indiana and the Kansas City metro area. The Consulate General is part of a worldwide network of Canadian diplomatic and trade offices, including more than 15 across the United States. In the Midwest, Canada accounts for more than 35% of the region's international trade. Canada is the largest export market for Illinois, Missouri and Wisconsin, larger than Mexico, China, Brazil, Australia and Japan combined. The Midwest–Canada trade relationship is worth more than $60 billion annually and supports more than 650,000 Midwest jobs. Canada is also the largest foreign supplier of oil, natural gas, electricity and uranium to the U.S. The trade partnership, along with an integral energy relationship, a shared responsibility for the Great Lakes and the environment, and the vast cultural, academic and tourism ties between the two countries, are just a few examples of why the Canada–U.S. relationship is so beneficial and meaningful to both nations. The mission's 27 staff members in Chicago work to further this relationship by promoting Canada's interests in this region through stronger trade and economic ties, as well as enhanced political, academic and cultural links between Canada and the Midwest. The Consulate General also provides consular assistance to Canadians who are visiting or living in the accredited territory.

The Two Prudential Plaza is a 64-story skyscraper located in the Loop area of Chicago, Illinois, United States. At 995 feet (303 m) tall, it is currently the sixth-tallest building in Chicago and the 28th-tallest in the U.S., being only five feet from 1,000 feet, making it the closest of any building under 1,000. Built in 1990, the building was designed by the firm Loebl Schlossman & Hackl, with Stephen T. Wright as the principal in charge of design. It has been honored with 8 awards, including winning the Best Structure Award from the Structural Engineers Association of Illinois in 1995.

Illinois Center is a mixed-use urban development in downtown Chicago, Illinois, USA, lying east of Michigan Avenue. It is notable in that the streets running through it have three levels. Elsewhere in Chicago, some streets have two levels, with the lower level for through traffic and service vehicles and the upper level for other local traffic. In Illinois Center, the lower level has been split, with a middle level for through traffic and a lower level for service vehicles. The development was built on land that had formerly been used for railroad yards by the Illinois Central Railroad, which merged into the Canadian National Railway in 1999. The earliest building is One Illinois Center designed by Ludwig Mies van der Rohe and completed in 1970. The west half of the rail yards were built out first; the east half was for a time turned into a temporary golf course on the lowest level, where the rail yards had been. The golf course has since been turned into a park, now surrounded by an urban village of high-rise buildings called Lakeshore East. The development consists of four blocks with a large area to the east. It is bounded on the west by Michigan Avenue, which has two levels. Just east of that road, the upper level rises to become a higher third level, only accessible on the west edge of the development and at the east end of Upper Wacker Drive. Stetson Avenue and Columbus Drive run north-south, and Lake Street, South Water Street, and Wacker Drive run east-west. Randolph Street lies a block south of the main part, and forms the south border of the east half. All of these streets are at least partly triple-decker. In the south half of the complex, the Metra Electric Lines and the South Shore Line terminate, halfway between Michigan and Stetson Avenues, at Millennium Station. An additional structure, Boulevard Towers East an 80-story mixed-use building was planned on the west side of Stetson between South Water and Lake Street but was cancelled. The site of this proposed building is the last remaining vacant lot in the Illinois Center complex, referred to by locals as the "Political Graveyard". Also proposed for this site was Mandarin Oriental Chicago. On February 18, 2009, a report in Crain's Chicago Business stated that a New York-based lender had filed a foreclosure suit against the developer, that the sale's center was closed and building units were no longer being marketed through the Multiple Listing Service. The project is no longer listed on the developer's website. One Prudential Plaza, Two Prudential Plaza and the Aon Center are in the blocks south of the main part.

McDonald's Cycle Center (formerly Millennium Park Bike Station) is an indoor bike station in the northeast corner of Millennium Park in the Loop community area of Chicago, in the U.S. state of Illinois. The city of Chicago built the center at the intersection of East Randolph Street and Columbus Drive, and opened it July 2004. Since June 2006, it has been sponsored by McDonald's and several other partners, including city departments and bicycle advocacy organizations. The bike station, which serves bicycle commuters and utility cyclists, provides lockers, showers, a snack bar with outdoor summer seating, bike repair, bike rental and 300 bicycle parking spaces as of 2004. The Cycle Center is accessible by membership and day pass. It also accommodates runners and inline skaters, and provides space for a Chicago Police Department Bike Patrol Group.Planning for the Cycle Center was part of the larger "Bike 2010 Plan", in which the city aimed to make itself more accommodating to bicycle commuters. This plan (now replaced by the "Bike 2015 Plan") included provisions for front-mounted two-bike carriers on Chicago Transit Authority (CTA) buses, permitting bikes to be carried on Chicago 'L' trains, installing numerous bike racks and creating bicycle lanes in streets throughout the city. Additionally, the Chicago metropolitan area's other mass transit providers, Metra and Pace, have developed increased bike accessibility. Chicago Mayor Richard M. Daley was an advocate of the plan, noting it is also an environmentally friendly effort to cut down on traffic. McDonald's controversially claimed that, since it is providing a healthier menu and fostering grade school physical education in an effort to help its customers improve their health, sponsoring bicycle and exercise activity in the park augments the company's other initiatives.Environmentalists, urban planners and cycling enthusiasts around the world have expressed interest in the Cycle Center, and want to emulate what they see as a success story in urban planning and transit-oriented development. Pro-cycling and environmentalist journalists in publications well beyond the Chicago metropolitan area have described the Cycle Center as exemplary, impressive, unique and ground-breaking.

One Prudential Plaza (formerly known as the Prudential Building) is a 41-story structure in Chicago completed in 1955 as the headquarters for Prudential's Mid-America company. It was the first skyscraper built in Chicago since the Great Depression of the 1930s and the Second World War. The plaza, including a second building erected in 1990, is owned by BentleyForbes and a consortium of New York investors, since the Great Recession of the early 21st century.

The Blue Cross Blue Shield Tower (BCBS) is on the north end of Millennium Park along E. Randolph Street at the NE corner of Randolph and Columbus Drive, in Chicago, Illinois, United States of America. It is home to the headquarters of Health Care Service Corporation. The building's address is 300 E. Randolph Street and is next to the Aon Center. Original plans to connect the two buildings via an underground pedway never came to fruition. Architect James Goettsch of Goettsch Partners designed the building. The 33-story first phase was completed in 1997 under the firm name of Lohan Associates (now Goettsch Partners). The 24-story second phase started in 2007 and was completed in 2010.

Great Central Station, also known as Great Central Depot, was an intercity train station in Chicago, Illinois owned by the Illinois Central Railroad (IC). It opened in 1856 and for a time was the largest building in downtown Chicago. Its passenger depot building was located on Water Street. In offices above the depot the IC had its headquarters, while beyond the depot was the large rail house where eight track lines ran. It was damaged in the Great Chicago Fire of 1871 but remained in operation. The station proved inadequate to handle growing traffic and its original building was demolished in 1893 in favor of the new Central Station further south. Although it continued to receive some traffic, over-time it increasingly became a commuter rail depot. Millennium Station, formerly Randolph Street Terminal, sits on the location.

Millennium Station (formerly Randolph Street Terminal; sometimes called Randolph Street station or Randolph/South Water Street station) is a major commuter rail terminal in the Loop (downtown), Chicago. It is the northern terminus of the Metra Electric District to Chicago's southern suburbs, and the western terminus of the South Shore Line to Gary and South Bend, Indiana. Located under Millennium Park, the terminal is a stub-end station and was established in the 1800s by the Illinois Central Railroad (IC) and has gone through several re-configurations. Most recently, it was rebuilt in the early 21st century and is owned by Metra through its operating arm, the Northeast Illinois Regional Commuter Railroad Corporation. Not counting commuters on the South Shore Line, over 18,000 people board Metra trains at Millennium Station each day. During peak periods, trains leave the terminal as frequently as twice a minute. It is the third-busiest train station in Chicago.

Jay Pritzker Pavilion, also known as Pritzker Pavilion or Pritzker Music Pavilion, is a bandshell in Millennium Park in the Loop community area of Chicago in Cook County, Illinois, United States. It is located on the south side of Randolph Street and east of the Chicago Landmark Historic Michigan Boulevard District. The pavilion was named after Jay Pritzker, whose family is known for owning Hyatt Hotels. The building was designed by architect Frank Gehry, who accepted the design commission in April 1999; the pavilion was constructed between June 1999 and July 2004, opening officially on July 16, 2004. Pritzker Pavilion serves as the centerpiece for Millennium Park and is the home of the Grant Park Symphony Orchestra and Chorus and the Grant Park Music Festival, the nation's only remaining free outdoor classical music series. It also hosts a wide range of music series and annual performing arts events. Performers ranging from mainstream rock bands to classical musicians and opera singers have appeared at the pavilion, which even hosts physical fitness activities such as yoga. All rehearsals at the pavilion are open to the public; trained guides are available for the music festival rehearsals, which are well-attended. Millennium Park is part of the larger Grant Park. The pavilion, which has a capacity of 11,000, is Grant Park's small event outdoor performing arts venue, and complements Petrillo Music Shell, the park's older and larger bandshell. Pritzker Pavilion is built partially atop the Harris Theater for Music and Dance, the park's indoor performing arts venue, with which it shares a loading dock and backstage facilities. Initially the pavilion's lawn seats were free for all concerts, but this changed when Tori Amos performed the first rock concert there on August 31, 2005. The construction of the pavilion created a legal controversy, given that there are historic limitations on the height of buildings in Grant Park. To avoid these legal restrictions, the city classifies the bandshell as a work of art rather than a building. With several design and assembly problems, the construction plans were revised over time, with features eliminated and others added as successful fundraising allowed the budget to grow. In the end, the performance venue was designed with a large fixed seating area, a Great Lawn, a trellis network to support the sound system and a signature Gehry stainless steel headdress. It features a sound system with an acoustic design that replicates an indoor concert hall sound experience. The pavilion and Millennium Park have received recognition by critics, particularly for their accessibility; an accessibility award ceremony held at the pavilion in 2005 described it as "one of the most accessible parks – not just in the United States but possibly the world".

Michigan Plaza is a two-tower office complex in the Chicago Loop area of Chicago, Illinois, United States. The complex is managed and leased by MB Real Estate.The complex consists of the 44-story 205 North Michigan Avenue and the 25-story 225 North Michigan Avenue and was designed by architect Fujikawa Johnson & Associates. The builders were inspired by the works of Ludwig Mies van der Rohe.