The Illinois Department of Transportation (IDOT) will handle many upcoming projects due to the recent statewide infrastructure strategic plan and the fast-track efforts affecting many infrastructure projects amid COVID-19. Nevertheless, many change orders are anticipated to occur on IDOT's projects. Thus, this paper examines the proper contractual management of changes within IDOT infrastructure transportation projects by following a research method based on the integration between a desktop analysis and a focus group analysis. The desktop analysis involved collecting information and data from existing resources, case studies, and documents related to change orders. The focus group analysis involved consulting with change order experts to verify that the outcome of each research step is useful and to validate the final outcomes of the paper. Based on 50 documented major change orders in IDOT projects and three litigated cases, two findings are provided. First, the top causes for key change orders within IDOT projects include contract administration, allowable contingencies, quantity omission or error, differing site conditions, and design changes. Second, the most critical change order related challenges within IDOT's infrastructure projects include approval procedures, compensation considerations, and applicable laws. This paper offers flowcharts, synopsis of opportunities and risks, and a checklist to help the contracting parties better administer change orders. Ultimately, the contributions of this paper to the practice include: (1) minimizing the number and amount of change orders, (2) helping the contracting parties better understand how their individual responsibilities contribute to the proper processing and management of changes and variations, (3) offering contractors the ability to visualize the different steps involved in the approval of change orders, (4) assisting the project stakeholders in identifying change order-related areas for improvement, and (5) allowing project owners to better mitigate, manage, and administer the contractual aspects of change orders.