Good question, Brad, and one I’ve wondered about in the past. So far, I look at it this way: People living in rural Mississippi often (maybe usually) did not have electricity, or money. People living in Chicago had plenty of electricity, and at least some money. I figure that had a lot to do with the musical styles of both areas. Also the lifestyles in those areas were quite different. In my minds eye, I see blues musicians in Mississippi sitting around on some front porch playing acoustic instruments – guitars, harmonicas, washboard bass – grandma sitting in her rocking chair nodding her head in time, kids dancing to the beat in the front yard. And I see blues musicians in Chicago jamming in some crowded club full of cigarette smoke, where they have to play loud to drown out the crowd noise. So I ask myself, what kind of music would I play in those circumstances?

Hey Brad,
I’m no expert but with Chicago Blues, Buddy Guy comes to mind. With Delta, Robert Johnson. This is just a general thought because most of the older guys started in the south and then spread out. See BB King and many more. Check out Jontavious Willis who was born in Georgia but got famous in Clarksdale Miss known as the home of the blues. (crossroads). He does Delta and just about everything else.
Do a search in lessons box for Delta blues and the Chicago Blues. Brian has lots of each. 🎸😊

Delta Blues: Son House “Death Letter Blues” (on YT)

Chicago: Muddy, Wolf, Buddy Guy (Anything by these guys)