"Easiest way into downtown from the East Side."
Picking up Emerson and running through downtown, all the way up to the North Side, Michigan Street is the easiest way I've found of entering downtown from the near East-Side. It crosses nearly every street of interest downtown, including Massachusetts Avenue and Meridian, and runs straight through the campus of IUPUI, where I attend college. Traffic usually flows very well, barring the occasional train that creates a back-up. New York runs parallel to Michigan in the opposite direction, and between these two streets, you can never be lost downtown. Just find one, and you will immediately know which direction is "home", or in the case of the visitor, "the hotel".