Monitoring maritime oil flow is important for the security and stability of energy transportation, especially since the “21st Century Maritime Silk Road” (MSR) concept was proposed. The U.S. Energy Information Administration (EIA) provides public annual oil flow data of maritime oil chokepoints, which do not reflect subtle changes. Therefore, we used the automatic identification system (AIS) data from 2014 to 2016 and applied the proposed technical framework to four chokepoints (the straits of Malacca, Hormuz, Bab el-Mandeb, and the Cape of Good Hope) within the MSR region. The deviations and the statistical values of the annual oil flow from the results estimated by the AIS data and the EIA data, as well as the general direction of the oil flow, demonstrate the reliability of the proposed framework. Further, the monthly and seasonal cycles of the oil flows through the four chokepoints differ significantly in terms of the value and trend but generally show an upward trend. Besides, the first trough of the oil flow through the straits of Hormuz and Malacca corresponds with the military activities of the U.S. in 2014, while the second is owing to the outbreak of the Middle East Respiratory Syndrome in 2015.