In a small saucepan, combine all the ingredients for the Jack Daniel's glaze. Bring the mixture to a boil over medium-high heat, stirring occasionally. Reduce the heat to low and simmer for 10-15 minutes or until the glaze has thickened. Set aside.
Preheat the grill over medium-high heat.
Divide the ground beef into 4 equal portions and shape them into patties. Make a slight indentation in the center of each patty to prevent it from puffing up during cooking. Season both sides of the patties with salt and black pepper.
Cook the patties for about 4-5 minutes on each side for medium doneness, or until they reach your desired level of doneness.
During the last minute of cooking, brush the top of each patty generously with the Jack Daniel's glaze and place a slice of cheddar cheese on top. Close the grill lid to allow the cheese to melt.
Remove the patties from the grill and let them rest for a couple of minutes.
Assemble the burgers by placing a patty on the bottom half of each toasted bun. Top each patty with two strips of crispy bacon, lettuce, tomato, red onion, and dill pickle chips. Drizzle additional Jack Daniel's glaze over the toppings, if desired.
Place the top half of the bun on the burger and serve immediately.