Many people in Chicago make money by working in the trade, transportation, and utilities industry which is the city's largest employer. If you want to make a lot of money in Chicago, you should consider joining the finance industry.  The Bureau of Labour Statistics estimates that securities and financial service sales agents are Chicago’s highest earners, making about $46.57 an hour. If this is not an option, consider getting a second job as most companies in the city have improved their minimum wages, bonuses, and benefits.