The Ventra Program has been at the cutting edge of fare collection innovation since 2013, from being one of the first account-based systems in the country allowing open payments, to a partnership with Apple and Google allowing you to tap your cell phone to pay for transit via the Ventra Mobile App and Digital Wallets. Now, Ventra is in the design and build phase of a project that will move the entire system to the cloud and enable even more convenience for Chicago transit riders. We will present a timeline to walk though the evolution of Ventra and into the future leveraging partnerships and innovation.