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Chicago is a city of precarious economic circumstances. Although the city has one of the largest metropolitan economies in the United States, it also has high, outstanding long-term debt, the highest per-person pension debt among the nation’s largest cities, and high outflows of high-income taxpayers leaving the city. While Chicago’s many economic opportunities and amenities are attracting a migration of young adults to the city, this debt and loss of income tax requires Chicagoans to pay more fees and taxes than any other city in the United States. Young adults are impacted differently by this paradox of economic opportunity and debt in the city.