Requiring a Canterbury Tales analysis can be difficult. Making the Canterbury Tales analysis part of an art project makes it easier.
One way I enrich students with information contained in the Prologue is to make them draw the pilgrims according to the details and description that Chaucer sets forth in the Prologue.
Not only do students have to pay attention to the details that are presented, but I make them rewrite the description into modern language and attach that to their drawing of the pilgrims. In other words, students have to engross themselves into Middle English, understand the text enough to draw their own rendering on the pilgrim, and then, students have to translate the Middle English language into their own vernacular.
I require that students draw at least four pilgrims from The Canterbury Tales and require them to write a ten-line description of each pilgrim that they select to draw.