Spicy Dill Pickle Grilled Cheese with Tomato Soup

Servings

Prep Time

20 minutes

Cook Time

1 hours

Cuisine

American

Ingredients

Tomato Soup

3 pounds ripe tomatoes, halved (quarter large tomatoes)
1 large yellow or white onion, roughly chopped
4–6 garlic cloves, peeled
3 tablespoons olive oil
2 tablespoons balsamic vinegar
Salt and black pepper, to taste
¼ cup fresh basil leaves
1–2 cups vegetable or chicken broth, as needed
¼ cup heavy cream, optional (or more to taste)

Grilled Cheese

8 slices sourdough bread or another thick, hearty bread
12 ounces Spicy Dill Pickle Jack Cheese, shredded or thinly sliced (3 cups)
20 crinkle-cut dill pickle chips
4 tablespoons softened butter

Directions

Tomato Soup

Preheat the oven to 400°F. Arrange the tomatoes, onion, and garlic on a large rimmed baking sheet. Drizzle with olive oil and balsamic vinegar, and generously season with salt and pepper.
Roast for 45-60 minutes, until the tomatoes and onions are softened.
Transfer the roasted tomatoes, onion, garlic, and any juices from the pan to a blender with the basil. Blend until smooth. Alternatively, add everything to a pot and use an immersion blender.
Warm the soup in a pot over medium-low heat. Add broth as needed to reach your desired consistency. Mix in heavy cream, and taste and adjust the salt and pepper before serving.
Serve with a drizzle of olive oil and more heavy cream, if desired.

Grilled Cheese

Pat the pickle chips dry with a paper towel. Divide half of the cheese between 4 slices of bread, followed by the pickles and remaining cheese. Top with the remaining 4 slices of bread.
Spread the outside of each sandwich with softened butter.
Heat a large skillet over medium-low heat. Cook the sandwiches for 3–4 minutes per side, or until the bread is golden brown and the cheese is completely melted. Work in batches if needed, and lower the heat if the bread is browning too quickly.
Slice each sandwich in half and serve while the cheese is warm and gooey.

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Article: Spicy Dill Pickle Grilled Cheese with Tomato Soup

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Oct 6, 2026

Spicy Dill Pickle Grilled Cheese with Tomato Soup

Name: Spicy Dill Pickle Grilled Cheese with Tomato Soup
Prep time: 20 min
Cook time: 1 h
Total time: 1 h 20 min
Yield: 4
Cuisine: American
Ingredients: 3 pounds ripe tomatoes, halved (quarter large tomatoes); 1 large yellow or white onion, roughly chopped; 4–6 garlic cloves, peeled; 3 tablespoons olive oil; 2 tablespoons balsamic vinegar; Salt and black pepper, to taste; ¼ cup fresh basil leaves; 1–2 cups vegetable or chicken broth, as needed; ¼ cup heavy cream, optional (or more to taste); 8 slices sourdough bread or another thick, hearty bread; 12 ounces Spicy Dill Pickle Jack Cheese, shredded or thinly sliced (3 cups); 20 crinkle-cut dill pickle chips; 4 tablespoons softened butter

Written by Meister Cheese

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