Preheat the oven to 375 degrees. Line a baking sheet with parchment paper. Place a pint-size Mason jar or glass in the center of the baking sheet; set aside.
To a large bowl, add cooked shredded chicken, chopped onion, red bell pepper, jalapeño, and taco sauce, stir to combine; set aside.
Cut tortillas in half. Place about 2 tablespoons each of the cheddar cheese, Monterey Jack cheese, and chicken mixture on each tortilla half. Roll the tortillas into cones, starting from the cut edge and making sure not to push the ingredients out of the tortilla.
Place 13 filled cones (seam side down) around the jar to create a ring. The points of the cones should be touching the jar. Sprinkle cheddar and Monterey Jack cheese over the layer. Repeat with the remaining cones to make 2 more layers, finishing with the rest of the cheddar and Monterey Jack. Remove the jar from the center of the ring before baking.
Bake until the cheese is melted and the edges of the tortillas are crispy, 15-20 minutes.
Carefully transfer the blooming quesadilla to a serving platter OR serve from the baking tray. Place your dip of choice inside the ring and top with fresh chopped cilantro. Serve immediately