Dry shrimp with paper towels and season with salt and pepper.
Add 1 tablespoon olive oil to a large, ovenproof skillet over high heat. Swirl to coat. When shimmering, add shrimp in an even layer. Cook, turning once, until lightly seared, about 1 ½ minutes per side. Add additional 1 tablespoon olive oil halfway through cooking if skillet is dry. Remove shrimp to a plate. Reduce heat to medium-high and add 2 tablespoons olive oil. Add fennel, garlic, chile flakes. Season with salt and pepper and cook until softened and golden in spots, about 4 minutes. Add orzo, chickpeas, cherry tomatoes, olives, dill, and lemon zest. Stir to combine. Add white wine and let reduce for 30 seconds. Add chicken broth, stir to combine, and return shrimp to skillet, nestling them into as even a layer as possible. Bring to a boil and transfer to oven. Bake 4 minutes, stir gently, and continue baking until orzo is cooked through, about 4 minutes more.
Serve immediately, drizzled with olive oil and topped with additional dill, lemon wedges, and feta.