Just asking for Alexa to play your favorite content can sometimes be frustrating. You don't always get what you ask for. Part of this has to do with the way that Alexa has thousands of ways to play your favorite content built in. If you enable the 97.1fm The Drive - WDRV Chicago Alexa skill you will have one command that will always work.
How do I know if I'm listening to the skill?
If you hear the 97.1fm The Drive - WDRV Chicago sounder before the stream begins, you are listening via the skill.