Preheat oven to 400 degrees F. Heat olive oil in a cast-iron or regular skillet over medium heat. Add bell pepper, onions, garlic, corn, jalapeños (if using), salt and pepper. Cook for 3 to 5 minutes.
In a medium bowl, combine cream cheese, mayo, sour cream, green chiles (if using), Worcestershire sauce and crab meat. Mix well and add to the skillet. Stir until combined.
If using a cast-iron skillet, spread dip in an even layer, top with shredded cheese and remove from heat. If not using a cast-iron skillet, coat a square baking dish with cooking spray and add the contents of the skillet topped with shredded cheese.
Bake uncovered in the preheated oven for 20 minutes or until bubbly. Serve with tortilla chips.