Electrical networks across the globe are gearing towards environmentally friendly operation with many renewable sources being introduced. Among them, the popularity of electrical generation by wind has gained the most ground. Wind, as one of the meteorological conditions, also has high influence on line ratings and such manner of operating the line is known as dynamic thermal rating (DTR) system. Seeing this relationship, it is intuitively important to investigate the reliability of a electrical network incorporating DTR and wind farm. Hence, the objective of this paper is to propose a methodology that can perform this task. In the methodology, sequential Monte Carlo (SMC) simulation was performed due to time dependencies of line ratings and wind power. As a result, modeling of these time-series data was performed using the auto-regressive and moving-average (ARMA) model. Moreover, correlations between line rating and wind power were also considered to provide a practical approach to the modeling. Results have shown that DTR system is able to increase network reliability and allows for higher wind energy penetration.