Municipal inspections are an important part of maintaining the quality of goods and services. In this paper, we approach the problem of intelligently scheduling service inspections to maximize their impact, using the case of food establishment inspections in Chicago as a case study. The Chicago Department of Public Health (CDPH) inspects thousands of establishments each year, with a substantial fail rate (over 3,000 failed inspection reports in 2023). To balance the objectives of ensuring adherence to guidelines, minimizing disruption to establishments, and minimizing inspection costs, CDPH assigns each establishment an inspection window every year and guarantees that they will be inspected exactly once during that window. Meanwhile, CDPH also promises surprise public health inspections for unexpected food safety emergencies or complaints. These constraints create a challenge for a restless multi-armed bandit (RMAB) approach, for which there are no existing methods. We develop an extension to Whittle index-based systems for RMABs that can guarantee action window constraints and frequencies, and furthermore can be leveraged to optimize action window assignments themselves. Briefly, we combine MDP reformulation and integer programming-based lookahead to maximize the impact of inspections subject to constraints. A neural network-based supervised learning model is developed to model state transitions of real Chicago establishments using public CDPH inspection records, which demonstrates 10% AUC improvements compared with directly predicting establishments' failures. Our experiments not only show up to 24% (in simulation) or 33% (on real data) objective improvements resulting from our approach and robustness to surprise inspections, but also give insight into the impact of scheduling constraints.