Recipes Soups Vegetable Soups Grilled Cheese with Creamy Tomato Soup

Grilled Cheese with Creamy Tomato Soup

Prep Time: 55 minutes
Cook Time: 60 minutes
Servings: 4

Many Americans have vivid memories of eating grilled American cheese sandwiches and bowls of canned tomato soup when they were kids. Here, that same classic pairing features the best Cheddar cheese and sourdough bread or pain au levain in the sandwiches and roasted tomatoes in the soup, for an over-the-top treat.


For the creamy tomato soup:

  • 4 lbs. plum tomatoes
  • 2 Tbs. olive oil
  • 1 Tbs unsalted butter
  • 2 stalks celery, finely chopped
  • 1/3 cup shallots, finely chopped
  • 1/2 cup chicken stock or broth, or as needed
  • 1 tsp. fresh thyme
  • 1/2 tsp. sugar
  • 1/2 cup heavy cream
  • Kosher salt and freshly ground pepper

For the grilled cheese:

  • 3/4 lb. mild cheddar cheese, thinly sliced
  • 8 slices sourdough bread or pain au levain
  • 4 Tbs. unsalted butter, at room temperature


To make the soup, preheat an oven to 400°F. Lightly oil a rimmed baking sheet. Cut the tomatoes in half lengthwise. Place them, cut side up, on the prepared baking sheet and brush with the 2 Tbs. oil. Roast until the tomatoes look somewhat shriveled, about 45 minutes. Let cool for about 20 minutes. Transfer the tomatoes and any juices to a food processor. Pulse until chopped, then rub the tomatoes and their juices through a coarse-mesh sieve placed over a bowl. You should have about 3 1/2 cups tomato purée. Discard the contents of the sieve.

In a large saucepan, melt the butter over medium-low heat. Add the celery and cook, stirring occasionally, until tender, about 5 minutes. Add the shallots and cook, stirring occasionally, until softened, about 3 minutes. Stir in the tomato purée, 1/2 cup stock, and the thyme and bring to a simmer over medium-high heat. Reduce the heat to medium-low and simmer, uncovered, for about 15 minutes. Stir in the sugar. In 3 or 4 batches, transfer the soup to a blender and process until smooth. Transfer to a clean saucepan, add the cream and heat until piping hot but not boiling. If the soup seems thick, thin with more stock. Season to taste with salt and pepper.

To make the grilled cheese sandwiches, heat a griddle or 2 large frying pans over medium heat until hot. For each sandwich, place one-fourth of the cheese on top of 1 bread slice and top with a second bread slice. Spread the outsides of each sandwich with 1 tablespoon of the butter. Place on the griddle, reduce the heat to medium-low and cook until the undersides are golden brown, 3–4 minutes. Flip the sandwiches and brown the other side, 3–4 minutes more. Ladle the soup into warmed bowls. Serve at once, with the hot sandwiches alongside. Serves 4.

Variation: Grilled cheese sandwiches offer countless variations. Switch it up by using your favorite bread or different cheeses. For an over-the-top sandwich, add ham and tomato slices before grilling.

Adapted from Williams-Sonoma Comfort Food, by Rick Rodgers (Oxmoor House, 2009)