Kenosha ( kə-NOH-shə) is a city in and the county seat of Kenosha County, Wisconsin, United States. Kenosha is on the southwestern shore of Lake Michigan. As of the 2020 census the population was 99,986, which made it the fourth-largest city in Wisconsin and the fourth-largest city on Lake Michigan. Although closer to Milwaukee, the city is part of the United States Census Bureau's Chicago combined statistical area (CSA) and metropolitan statistical area. Once a center of industrial activity, its gradual transition into a hub for the services-based economy of today has made it a bedroom community within the Chicago and Milwaukee metro areas. Kenosha is home to multiple educational institutions including the University of Wisconsin–Parkside, Carthage College, and Gateway Technical College. It is home to the headquarters of the Fortune 1000 tool manufacturer Snap-on Inc., as well as the clothing company Jockey International. Residents of the city are called Kenoshans.

Bordering Chicago along Lake Michigan, Chicago’s North Shore is the most picturesque region in the metropolitan Chicago area boasting a scenic byway along the lakefront rich in natural beauty and homes and gardens of distinction.

Racine ( rə-SEEN) is a city in and the county seat of Racine County, Wisconsin, United States. It is located on the shore of Lake Michigan at the mouth of the Root River. Racine is situated 22 miles (35 km) south of Milwaukee and approximately 70 miles (112 km) north of Chicago. It is the principal city of the US Census Bureau's Racine metropolitan area (consisting only of Racine County). The Racine metropolitan area is, in turn, counted as part of the Milwaukee combined statistical area. As of the 2010 U.S. Census, the city had a population of 78,860, making it the 5th largest city in Wisconsin. Its median home price of $103,625 makes it one of the most affordable cities in Wisconsin to buy a home. In January 2017, it was rated "the most affordable place to live in the world" by the Demographia International Housing Affordability survey.Racine is the headquarters of a number of industries, including J. I. Case heavy equipment, S. C. Johnson & Son cleaning and chemical products, Dremel Corporation, Reliance Controls Corporation time controls and transfer switches, Twin Disc, and Arthur B. Modine heat exchangers. The Mitchell & Lewis Company, a wagonmaker in the 19th century, began making motorcycles and automobiles as Mitchell-Lewis Motor Company at the start of the 20th century. Racine is also home to InSinkErator, manufacturers of the first garbage disposal. Racine was also historically home to the Horlicks malt factory, where malted milk balls were first developed, and the Western Publishing factory where Little Golden Books were printed. Prominent architects in Racine's history include A. Arthur Guilbert and Edmund Bailey Funston, and the city is home to several works by Frank Lloyd Wright. It has several immigrant communities, and is among the most diverse cities in Wisconsin.

Rosemont is a village in Cook County, Illinois, United States. Located immediately northwest of Chicago, as of the 2010 census it had a population of 4,202. The village was incorporated in 1956, though it had been settled long before that. While Rosemont's land area and population are relatively small among municipalities in the Chicago Metropolitan Area, the village is a major center for commercial activity in the region and is a key component of the Golden Corridor. Due to its proximity to several interstates, O'Hare International Airport, and downtown Chicago, it has emerged as a significant edge city and entertainment district, with corporate facilities, millions of square feet of office space, nearly 50 restaurants, 15 hotels, the 840,000-square-foot (78,000 m2) Donald E. Stephens Convention Center (home to conventions and trade shows), the 16,000+ seat Allstate Arena (home to the Chicago Wolves, Chicago Sky, DePaul Blue Demons until 2017, and concerts and other live entertainment events), the 4,000+ seat Rosemont Theatre, the 130-store Fashion Outlets of Chicago, the Rosemont Stadium (home to an outdoor collegiate-level softball stadium and 140,000 sq ft indoor sports dome), Impact Field (home to the Chicago Dogs independent minor league baseball team), and the entertainment complex Parkway Bank Park, which features restaurants, entertainment and a large common area used for summer concerts and ice skating in the winter. Rosemont is near Rivers Casino in Des Plaines and additional hotels, offices, restaurants, and corporate facilities in the adjacent O'Hare neighborhood of Chicago and nearby suburban communities such as Des Plaines and Schiller Park. The residential sections of Rosemont are a gated community, as a result of the 1995 decision by residents to enclose the residential portions of the village (roughly half the area of the village), thereby restricting access to locals.