Dill Pickle Grilled Cheese

This sandwich transforms the beloved classic dill pickle wrap into a melty, indulgent grilled cheese experience. The combination of tangy pickles, savory ham, and creamy cheese creates a flavor explosion that elevates the humble grilled cheese to something truly special.

I first made these sandwiches during a rainy weekend when my kids were craving something comforting yet different. Now they request these sandwiches weekly, especially after soccer practice when everyone needs a quick but satisfying meal.

Ingredients

• White or sourdough bread: Fresh bakery bread provides the best texture and flavor base for this sandwich
• Butter: Use softened butter for easy spreading and optimal browning
• Cream cheese: Creates a rich creamy layer that complements the tangy pickles perfectly
• Fontina cheese: Melts beautifully with a mild nutty flavor that doesn't overpower the other ingredients
• Thinly sliced ham: Adds savory protein. Look for quality deli ham rather than prepackaged for best results
• Kosher dill pickle sandwich slices: The star ingredient that brings brightness and crunch. Choose thick cut for texture

Step-by-Step Instructions

Prepare the bread:

Spread softened butter evenly across the outside of each bread slice. This creates that perfect golden crust when grilled. Then spread cream cheese on the inside of each slice, ensuring complete coverage to create a moisture barrier that prevents sogginess.

Layer the sandwich:

Place one slice of Fontina on the bottom piece of bread atop the cream cheese layer. This first cheese layer acts as an adhesive for the fillings. Arrange the ham slices evenly, followed by pickle slices, ensuring even distribution across the sandwich. Top with the second slice of Fontina, which helps seal everything together.

Grill to perfection:

Heat your skillet over medium-low heat. This slower cooking method allows the cheese to melt completely while giving the bread time to achieve that perfect golden brown exterior. Place the sandwich butter side down and cook patiently for 4-5 minutes until the bottom is golden and cheese begins melting. Flip carefully using a wide spatula to support the entire sandwich and cook the second side for 3-4 minutes until equally golden.

Serve immediately:

Remove from heat and slice diagonally for the most appealing presentation. The sandwich should be served immediately while the cheese is still delightfully melty and the bread remains crisp.

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The kosher dill pickles are truly the heart of this sandwich. My grandmother always had homemade pickles in her refrigerator, and incorporating them into this grilled cheese brings back memories of summer afternoons in her kitchen. The tanginess cuts through the rich cheese perfectly.

Make-Ahead Options

These sandwiches can be assembled up to 4 hours ahead of time before the grilling stage. Simply prepare as directed, then wrap tightly in plastic wrap and refrigerate. This makes them perfect for busy weeknights when you need to prep ahead. When ready to cook, simply unwrap and grill as directed, adding about 1 minute per side to account for the chilled ingredients.

Perfect Pairings

This sandwich stands beautifully on its own, but truly shines when paired with complementary sides. A cup of tomato soup creates the classic grilled cheese pairing experience with the pickle adding a unique twist. For a lighter option, serve with a simple green salad dressed with vinaigrette to balance the richness of the sandwich. During summer months, potato chips and a pickle spear on the side emphasize the dill flavor profile.

Ingredient Substitutions

Fontina cheese can be swapped for Havarti, Gouda, or even American cheese if you prefer. Each brings a slightly different flavor profile but all melt beautifully. Turkey works wonderfully in place of ham for a lighter option. If you prefer a spicier profile, consider adding pickled jalapeño slices alongside or in place of some of the dill pickles. For those who enjoy more texture, adding thin apple slices creates a delightful sweet-tart contrast.

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Frequently Asked Questions

→ Can I use a different type of cheese?

Yes, you can substitute Fontina with other melty cheeses like mozzarella, Gouda, or Swiss. Experiment to find your favorite combination!

→ What bread works best for this sandwich?

White bread or sourdough are ideal, but you can use any bread that toasts well, such as whole grain or gluten-free options.

→ Can I add other ingredients to the sandwich?

Absolutely! Consider adding bacon, spicy mustard, or even some thinly sliced onions for an extra punch.

→ How do I prevent the bread from burning?

Cook the sandwich over medium-low heat to avoid burning while allowing the cheese to melt fully.

→ Can I make this sandwich ahead of time?

It’s best served fresh, but you can prep the ingredients in advance. Assemble and grill just before serving for the best results.