Heat 1 tablespoon oil in 10-inch nonstick skillet over medium-high heat. Add fennel bulb; saute until beginning to brown, about 5 minutes. Cover and cook until softened, stirring occasionally, about 4 minutes. Add tomatoes and mash with fork; mix in olives. Season with salt and pepper. Transfer mixture to medium bowl. Add remaining 1 tablespoon oil to same skillet; heat over medium-high heat. Add beaten eggs and cook until eggs are just set in center, tilting skillet and lifting edges of omelet with spatula to let uncooked portion flow underneath, about 3 minutes. Sprinkle half of cheese over half of omelet, then top with fennel mixture. Sprinkle dill over, then remaining cheese. Using spatula, fold uncovered half of omelet over cheese; slide onto plate. Garnish with chopped fennel fronds and serve.