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Grilled Cheese with Caramelized Onions

The grilled cheese with caramelized onions is Chuck Hughes' divine tweaked version of the tried-and-true classic sandwich. Serve with Creamy Tomato Soup.
  • Level: Easy
  • Total: 45 min
  • Prep: 15 min
  • Cook: 30 min
  • Yield: 4 servings
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2 tablespoons/30ml olive oil

3 large onions, sliced

Salt and pepper

Salt and pepper 

8 thick slices bread

1/4 cup/60ml butter, room temperature

2 cups/500ml grated aged Cheddar

Serving suggestion: Creamy Tomato Soup, recipe follows

Creamy Tomato Soup:

2 tablespoons/30ml olive oil

2 cloves garlic, minced

1 medium onion, chopped

2 tablespoons brown sugar

12 large tomatoes, chopped

4 sprigs fresh thyme

1 piece Parmesan rind, optional

1/4 cup/60ml 35-percent cream

2 tablespoons/30ml butter

Salt and pepper

Grated Parmesan, for serving

Chopped fresh chives, for serving


  1. Heat the oil in a large skillet over medium heat. Saute the onions until soft and caramelized, about 25 minutes. Season with salt and pepper. Transfer the onions to a plate. 
  2. Generously butter both sides of each bread slice. In between two bread slices, pile the caramelized onions between two layers of cheese. 
  3. Heat a large skillet or griddle over medium-low heat. Cook the sandwiches, flipping once, until the cheese is melted and the bread is golden brown, 2 to 3 minutes per side.
  4. Serve with Creamy Tomato Soup.

Creamy Tomato Soup:

  1. Heat the oil in a large saucepan over medium heat. Add the garlic and onions and cook until the onions are translucent, about 5 minutes. Add the brown sugar and tomatoes and cook for 5 minutes more. Add 1/2 cup water, the thyme and Parmesan rind, if using. Cook for about 25 minutes.
  2. Discard the thyme sprigs and Parmesan rind. Puree the soup in a food processor or with an immersion blender until smooth. Strain through a fine sieve set over cleaned saucepan. Stir in the cream and butter. Season with salt and pepper. 
  3. To serve, ladle the soup into bowls and sprinkle with Parmesan and chives.