Preheat your oven to 375°F (190°C).
Lightly spray a muffin tin with cooking spray and press wonton wrappers into the tin. Bake for about 8-10 minutes until golden brown and crispy.
Season chicken breasts with salt and pepper, then grill or bake until cooked. Cool and cube.
In a large mixing bowl, combine chopped romaine, cubed chicken, and Caesar dressing. Toss well.
Once wonton cups are baked and cooled, fill each cup with the salad mixture.
Top with shaved parmesan, halved cherry tomatoes, and mini croutons. Serve immediately.