Settlements similar to or like Chicago

Central business district of the city and is the main section of Downtown Chicago. Second largest commercial business district in North America and contains the headquarters and regional offices of several global and national businesses, retail establishments, restaurants, hotels, and theaters, as well as many of Chicago's most famous attractions. Wikipedia

Capital and most populous city of the Commonwealth of Massachusetts in the United States and 21st most populous city in the United States. Estimated population of 692,600 in 2019, also making it the most populous city in New England. Wikipedia

Most populous city in the U.S. state of Texas, fourth-most populous city in the United States, most populous city in the Southern United States, as well as the sixth-most populous in North America, with an estimated 2019 population of 2,320,268. Seat of Harris County and the principal city of the Greater Houston metropolitan area, which is the fifth-most populous metropolitan statistical area in the United States and the second-most populous in Texas after the Dallas–Fort Worth metroplex, with a population of 7,066,141 in 2019. Wikipedia

Most populous city in the U.S. state of Maryland, as well as the 30th most populous city in the United States, with an estimated population of 593,490 in 2019. Largest independent city in the country and was designated as such by the Constitution of Maryland in 1851. Wikipedia

Largest city in the state of Wisconsin and the fifth-largest city in the Midwestern United States behind Chicago, Illinois; Columbus, Ohio; Indianapolis, Indiana; and Detroit, Michigan. On Lake Michigan's western shore. Wikipedia

State capital and most-populous city of the U.S. state of Indiana and the seat of Marion County. 886,220. Wikipedia

Capital and most populous city of the U.S. state of Georgia. Estimated 2019 population of 506,811, it is also the 37th most populous city in the United States. Wikipedia

Largest city in the Commonwealth of Kentucky and the 29th most-populous city in the United States. Historical seat and, since 2003, the nominal seat of Jefferson County, on the Indiana border. Wikipedia

Seaport city on the West Coast of the United States. Seat of King County, Washington. Wikipedia

Major city in the U.S. state of Ohio, and the county seat of Cuyahoga County. Located along the southern shore of Lake Erie, across the U.S. maritime border with Canada and approximately 60 mi west of the Ohio-Pennsylvania state border. Wikipedia

Largest and most populous city in the U.S. state of Oregon and the seat of Multnomah County. Major port in the Willamette Valley region of the Pacific Northwest, at the confluence of the Willamette and Columbia rivers in Northwestern Oregon. Wikipedia

Most populous city in the U.S. state of South Dakota and the 139th-most populous city in the United States. County seat of Minnehaha County and also extends into Lincoln County to the south, proximate with the Iowa state line. Wikipedia

Second-largest city in Missouri, and sits on the western bank of the Mississippi River, which forms the state line between Illinois and Missouri. The Missouri River merges with the Mississippi River 15 river miles north of Downtown St. Louis, forming the fourth-longest river system in the world. Wikipedia

Third-largest city in the United States and a major transportation hub for the Midwest. Served by two major airports, and is the main freight rail hub of North America. Wikipedia

Most populous city in the US state of Minnesota and the seat of Hennepin County. Estimated population of 429,606 as of 2019, it is the 46th most populous city in the US. Wikipedia

Most populous city in Florida, and is the largest city by area in the contiguous United States as of 2020. Seat of Duval County, with which the city government consolidated in 1968. Wikipedia

Capital and most populous city of the U.S. state of Tennessee. County seat of Davidson County and is located on the Cumberland River. Wikipedia

State capital and the most populous city in the U.S. state of Ohio. 14th-most populous city in the U.S., the second-most populous city in the Midwest after Chicago, and the third-most populous state capital. Wikipedia

Most populous city in the United States. Estimated 2019 population of 8,336,817 distributed over about 302.6 sqmi, New York City is also the most densely populated major city in the United States. Wikipedia

Capital and most populous city of the U.S. State of Colorado. Located in the South Platte River Valley on the western edge of the High Plains just east of the Front Range of the Rocky Mountains. Wikipedia

City in the state of Pennsylvania in the United States, and is the county seat of Allegheny County. An estimated population of about 300,286 residents live within the city limits as of 2019, making it the 66th-largest city in the U.S. and the second-most populous city in Pennsylvania, behind Philadelphia. Wikipedia

Public park located in the Loop community area of Chicago in Illinois operated by the Chicago Department of Cultural Affairs and managed by MB Real Estate. Intended to celebrate the third millennium and is a prominent civic center near the city's Lake Michigan shoreline that covers a 24.5 acre section of northwestern Grant Park. Wikipedia

Region generally covering the northern third of the U.S. state of Illinois. By far the most populous of Illinois with nearly 9.7 million residents as of 2010. Wikipedia

Capital and most populous city of the U.S. state of Utah, as well as the seat of Salt Lake County, the most populous county in Utah. Estimated population of 200,567 in 2019, the city is the core of the Salt Lake City metropolitan area, which has a population of 1,222,540 . Wikipedia