For the dip: Combine cream cheese, mayonnaise, onion, seasonings, and pimentos in a medium bowl and stir until evenly distributed. Fold in shredded cheddar, cover and refrigorate at least 4 hours, or overnight.
For the chips: Preheat oven to 350°F. Separate pita pockets into two rounds. Cut into 9ths and place in a large bowl. Drizzle with olive oil and toss until all pieces of pita are well coated. Dust with Cajun seasoning and toss until evenly distributed.
Lay out pitas in a single layer over a parchment lined sheet tray; use more than one tray if necessary to get a single layer. Bake until golden brown and allow to cool.
For service: Plate pimento dip as desired and serve along side cajun pita chips.
