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Chicago, officially the City of Chicago, is the most populous city in the U.S. state of Illinois, and the third-most-populous city in the United States. With an estimated population of 2,693,976 in 2019, it is also the most populous city in the Midwestern United States. Chicago is the county seat of Cook County, the second-most-populous county in the US, with a small portion of the northwest side of the city extending into DuPage County near O’Hare Airport. Chicago is the principal city of the Chicago metropolitan area, often referred to as Chicagoland. At nearly 10 million people, the metropolitan area is the third most populous in the United States. See more.
Madison is the capital of the U.S. state of Wisconsin and the seat of Dane County. As of July 1, 2019, Madison’s estimated population of 259,680 made it the second-largest city in Wisconsin by population, after Milwaukee, and the 82nd-largest in the United States. Madison is the fastest-growing city in Wisconsin. The city forms the core of the Madison Metropolitan Area which includes Dane County and neighboring Iowa, Green, and Columbia counties for a population of 654,230. See more.
Milwaukee is the largest city in the state of Wisconsin and the fifth-largest city in the Midwestern United States. The seat of Milwaukee County, it is on Lake Michigan’s western shore. Ranked by its estimated 2018 population, Milwaukee was the 31st largest city in the United States. The city’s estimated population in 2019 was 590,157. Milwaukee is the main cultural and economic center of the Milwaukee metropolitan area which had a population of 2,043,904 in the 2014 census estimate. It is the fourth-most densely populated metropolitan area in the Midwest, surpassed only by Chicago, Minneapolis-St. Paul and Detroit, respectively. Milwaukee is considered a “Gamma -“global city as categorized by the Globalization and World Cities Research Network with a regional GDP of over $105 billion. See more.