The growing importance of agriculture in the Brazilian economy makes it essential that agricultural companies seek to increase their logistics competitiveness. This study aimed to compare and analyze the impact of seasonality of grain harvest and specific events, such as the 2018 Brazil truck drivers’ strike, on the prices of inbound and outbound freight in a multinational company located in several Brazilian states. It focused on the CIF (Cost, Insurance, and Freight) routes of the company between 2015 and 2019 in Brazil, and the relationship between time of year and cost of transportation. These data were analyzed in a descriptive level after being treated by statistical analysis. This study showed that the costs of outbound freight suffered greater increases compared to the inbound freight due to the seasonality of grain harvest and the 2018 Brazil truck drivers’ strike.