In a large skillet over medium-high heat, heat oil. Add chicken and season with salt and pepper. Cook until golden and no longer pink, 8 minutes per side. Let rest 5 minutes, then slice.
Line a surface with a large square of parchment. Fold up bottom corner to make a triangle. Cover paper with 3 leaves romaine and top with 2 slices provolone, tomato, 2 slices bacon and cooked chicken slices, then drizzle with ranch and season with salt and pepper. Top with romaine leaf.
Roll wrap by folding sides in toward one another, then tightly wrap parchment paper around bottom. Poke with a toothpick and repeat with remaining ingredients to make three more wraps.