Helping Families Fly Act of 2019 This bill directs the Transportation Security Administration (TSA) to implement training for its frontline personnel regarding the screening of pregnant women and families with young children at passenger screening checkpoints, including (1) information related the use of advanced imaging technology on pregnant women, as well as opt-out and alternative screening procedures; and (2) guidelines and procedures for efficiently and respectfully screening pregnant women and families with young children. The TSA must also create a strategy for communicating procedures and guidelines to pregnant women and families with young children, including through social media, and its customer service call center; make passenger support specialists available to assist such women and families with screening checkpoint information; and assess the feasibility of developing dedicated screening lanes for such families.