16. Chicago, Illinois
Chicago continues to hold a spot among the most expensive major cities in the United States. Its high cost of living is driven primarily by powerful — and pricey — housing markets across both the city and surrounding suburbs.
While the city itself has a wide range of neighborhoods, many of Chicago’s affluent suburbs regularly top Illinois’s lists of most expensive places to live. The broader Chicago–Naperville–Elgin metro area essentially dominates the state’s upper-tier housing rankings.
Chicago’s status as a global city plays a major role. With world-class museums, top-tier dining, Fortune 500 headquarters, and cultural events, residents pay a premium for access to these amenities. Luxury high-rise condos, historic homes, and exclusive neighborhoods further contribute to Chicago’s elevated housing prices.
Suburban communities such as Winnetka and nearby affluent towns push median home values even higher, reinforcing the metro area’s reputation as one of the costliest in the Midwest.
