In a medium bowl, toss chicken with dressing, 2 tablespoons olive oil, and half of lemon juice.
Cover with plastic wrap and let marinate in fridge for at least 30.
Meanwhile, soak 12 bamboo skewers in water for 30.
Preheat a grill pan over medium-high heat.
Divide and thread chicken onto 6 skewers; season with salt and pepper.
In a medium bowl, toss bread with 2 tablespoons olive oil to coat.
Alternating with tomatoes, thread the bread and tomatoes onto remaining skewers.
Brush grill pan with olive oil.
Add the chicken skewers and grill until cooked through, about 10.
Remove and set aside.
Grill the bread and tomato skewers until charred and tomatoes begin to burst, about 5.
Top romaine leaves with chicken, croutons and tomatoes.
Drizzle with more dressing, sprinkle with Parmesan and squeeze lemon on top of each serving.