Boston is the capital of and largest city in Massachusetts, and is one of the oldest cities in the United States. The largest city in New England, Boston is regarded as the unofficial "Capital of New England" for its economic and cultural impact on the entire "New England" region. The city proper had a 2009 estimated population of 645,169, making it the twentieth largest in the country. It is also the anchor of a substantially larger metropolitan area called  "Greater Boston", home to 4.5 million people and the tenth-largest metropolitan area in the country. Greater Boston as a commuting region includes six Massachusetts counties:  "Essex", "Middlesex","Norfolk", "Suffolk", "Plymouth", "Worcester", northern "Bristol" County, all of "Rhode Island" and parts of "New Hampshire"; it is home to 7.6 million people, making it the fifth-largest Combined Statistical Area in the United States.

Washington, D.C., formally the District of Columbia and commonly referred to as Washington, the District, or simply D.C., is the capital of the United States founded on July 16, 1790. The U.S. Constitution allows for the creation of a special district to serve as the permanent national capital. The District is therefore not a part of any U.S. state and is instead directly overseen by the federal government. Within the District, a new capital city was founded in 1791 and named in honor of George Washington. The City of Washington, along with Georgetown and outlying areas within the federal district, were placed under a single, unified government following an act of Congress in 1871. It is for this reason that the city, while legally named the District of Columbia, is known as Washington, D.C. The city shares its name with the U.S. state of Washington located on the country's Pacific coast.

Hawaii is the newest of the 50 U.S. states (August 21, 1959), and is the only U.S. state made up entirely of islands. It is the northernmost island group in Polynesia, occupying most of an archipelago in the central Pacific Ocean, southwest of the continental United States, southeast of Japan, and northeast of Australia. Hawaii’s natural beauty, warm tropical climate, inviting waters and waves, and active volcanoes make it a popular destination for tourists, surfers, biologists, and volcanologists alike. Due to its mid-Pacific location, Hawaii has many North American and Asian influences along with its own vibrant native culture. Its capital is Honolulu on the island of Oʻahu.

Chicago is the largest city in the state of Illinois. Its metropolitan area, commonly named "Chicagoland", is the 27th most populous metropolitan area in the world, home to an estimated 9.7 million people spread across the U.S. states of Illinois, Indiana and Wisconsin. Chicago is the county seat of Cook County, the second largest county in the United States by population. The city is renowned for its fascinating museums - including the Art Institute and its expansive collections, including noted Impressionist works; it is a city with an appetite for food, of course, but also for design, history, culture, finance, commerce, industry, technology, telecommunications and transportation.