MAKE THE DRESSING:
In the bowl of a food processor, combine all of the ingredients except for 1/2 cup of blue cheese crumbles. Process the ingredients until the dressing is smooth then stir in the remaining 1/2 cup of blue cheese crumbles. (Alternately, you can whisk together the ingredients in a bowl until well combined.)
Taste and season the dressing with salt and pepper then set the dressing aside.
MAKE THE SALAD:
Add the bacon to a large sauté pan set over medium heat. Cook the bacon, draining the grease as needed, until all the fat has rendered. Using a slotted spoon, transfer the bacon to a paper towel-lined plate and reserve the bacon drippings.
Return about 2 tablespoons of the bacon drippings to the sauté pan then turn the heat to high. Add the cherry tomatoes and cook, stirring, until they are blistered. Remove the tomatoes from the heat.
To assemble the salad, place a dollop of dressing down on each plate. (This will ensure the iceberg wedge stays in place.) Set a wedge of lettuce on each plate and top it with the prepared dressing, tomatoes, bacon, croutons and chives.