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Preheat oven to 375°. On a rimmed baking sheet, toss bread with 1 teaspoon olive oil, ¼ teaspoon garlic powder, ¼ teaspoon salt, and ¼ teaspoon pepper. Spread in a single layer and bake until golden and crisp, 10 to 12 minutes.
Meanwhile, season chicken on all sides with oregano and remaining ½ teaspoon garlic powder, ½ teaspoon salt, and ½ teaspoon pepper. In a large skillet over medium-high heat, heat remaining 1 tablespoons oil until shimmering. Cook chicken, turning occasionally, until both sides have a nice sear and an instant-read thermometer inserted into thickest part of breast registers 165º, 2 to 3 minutes per side.
Transfer chicken to a cutting board. Once cool enough to handle, slice chicken into strips.
In a large bowl, toss chicken, croutons, lettuce, Parmesan, and desired amount of Caesar dressing; season with salt and pepper
Divide salad among tortillas and wrap up burrito-style. Slice in half and serve.