Preheat a grill or grill pan to medium. Place 4 soup bowls in the freezer. Thread the chile and garlic on a skewer. Brush the chile-garlic skewer, bell pepper and onion with 1 tablespoon olive oil. Grill until well marked, about 4 minutes per side. Add the bread halfway through and grill until toasted, about 2 minutes per side.
Transfer the grilled bell pepper, onion, chile and garlic to a blender. Add 6 cups cantaloupe, the vinegar and 2 tablespoons olive oil. Puree until smooth; season with salt and pepper. Transfer the soup to a medium bowl set inside a large bowl of ice to chill. Refrigerate, stirring occasionally, until cold, at least 10 minutes.
While the soup chills, spread the aïoli on the grilled bread and top with the ham. Finely dice the remaining 1 cup cantaloupe. Serve the soup in the chilled bowls and top with the diced cantaloupe, parsley and a few grinds of pepper. Drizzle with the remaining 1 tablespoon olive oil. Serve with the ham crostini.