Over two-thirds of all Illinois residents live in Chicago's metropolitan area. The third largest city in the United States and also the third most economically productive, the Windy City benefits from unrivalled industry diversity. Like any other city, however, Chicago faces the policy challenge of supporting well-paid employment opportunities for its residents. In spite of its economic dynamism, and although its population has grown slowly over the past decade, roughly half of Chicago's neighborhoods have youth unemployment rates of 20 percent or higher. Since the Great Recession, Chicago's city government and Illinois's state government have experimented with dozens of different strategies to support employment. Not all have had the desired impact. A 2015 analysis by the Illinois Economic Policy Institute (ILEPI) found that only four out of 24 different policy strategies studied directly supported employment: increased bachelor's degree attainment, better access to early childhood education and care, reduced commuting times, and improvements to transit infrastructure such as highways and bridges. In a more recent report, the same authors found evidence in favor of another policy strategy: increased investment in apprenticeship pathways. Because they are regular, paid employees from the start, apprentices can see the labor market value of their skills from day one. By learning on the job and taking technical coursework directly related to their work, which is usually provided at low or no cost, apprentices reap the employment and earnings benefits of higher education with less cost than traditional college. "Apprenticeship programs create pathways into middle-class careers for young adults who are unable or unwilling to go to college," wrote ILEPI's researchers in the 2020 report. Many successful apprentices, indeed, will enjoy higher lifetime returns from their educational programs than will associate degree and even some bachelor's degree graduates. To depict apprenticeship merely as an "alternative" to college, however, is an incomplete rendering. Apprenticeship works as an end in itself--especially in traditional apprenticeship occupations in the building trades, as ILEPI's authors describe--but can also serve as a bridge to further education, in some cases integrating completely with college degree programs. These nontraditional, college-connected apprenticeships, which use college coursework for their related technical instruction, provide a work-based pathway into well-paid careers in a number of professional fields that have historically required strictly academic training. The evolution of apprenticeship programs and the variety of their possible uses in municipal economic development strategies are nowhere as evident as in Chicagoland. The governments of the City of Chicago and Cook County have worked for decades to build policies and systems that incentivize apprenticeship training and equitable hiring in public and private development projects. Organized labor, commercial developers, and contractors, as well as the steadfast efforts of dozens of community-based organizations, all play important roles in Chicago's construction apprenticeship system. By sustaining traditional, non-college apprenticeships in the building trades, the city continues to address the underrepresentation of racial minorities in well-paid construction jobs. But more recently, Chicago has also led the way in the development of college-connected programs across a range of nontraditional apprenticeship occupations. Driven by the City Colleges of Chicago, a network of experienced workforce development advocates, and some of Chicago's largest white-collar employers, these innovative college-connected apprenticeships in business services, information technology, and healthcare support employment and college attainment at the same time. Chicago's apprenticeship strategy is still evolving, but for municipal leaders looking to couple economic development with equitable workforce development, the city's support for traditional construction programs as well as nontraditional, college-connected apprenticeship pathways provides an instructive example.