Heat the olive oil in a large skillet over medium heat. Add the chorizo and cook, crumbling it as you go, until browned. Remove from the skillet and drain on a paper towel-lined plate. Pour off any excess fat from the skillet.
Add the onion and bell peppers to the skillet and cook over medium-high heat until the veggies begin to soften, about 5 minutes. Turn off the heat and stir in 1/4 cup of the tequila. Turn the heat back on and cook until the vegetables are golden brown, 2 to 3 minutes more. Remove from the heat and set aside.
Meanwhile, stir the tomatoes and remaining 1 tablespoon tequila together in a small bowl and set aside to marinate for a few minutes.
To build, cover the bottom of a medium ovenproof skillet with a third of the Monterey Jack and Cheddar. Add half of the chorizo, then another third of the cheese. Next, add as much of the veggie mixture as you'd like (you may have a little left over). Add almost all of the remaining cheese, the rest of the chorizo and then whatever cheese you have left. Sprinkle the top very lightly with chili powder.
Bake, starting to watch it 4 to 5 minutes in, until the cheese is totally melted, hot and slightly bubbling...but before the cheese starts to firm up/harden. (In other words, you still want the cheese to be extra gooey.)
Drain the tomatoes.
Remove the skillet from the oven and top with the spiked tomatoes and cilantro. Serve immediately with tortilla chips. It's best when piping hot! Wrap a cloth around the skillet handle so guests won't burn themselves.