Side wind effects on driving safety were investigated for long-span bridges in strong wind based on comprehensive management of freeway. Critical wind speeds of safety driving concerning four typical vehicles were analyzed with considering wind speed, vehicle dimensions, road surface condition and vehicle speed. In combination with statistics of on-situ wind speed observation data and interaction analysis of structures on natural wind, a probability model and evaluating method with the concept of effective wind speed on bridge deck were proposed for driving safety analysis. By using the evaluating method, driving safety issues on Hangzhou Bay Oversea Bridge and Sutong Yangtze Highway Bridge were investigated. Results show that side slip is the main issue of driving safety while the vehicles pass by the bridge pylons in strong wind conditions.