There is nothing more comforting than a bowl of soup on a cold day. Plus, this roasted tomato soup gets topped with the cutest grilled cheese croutons you ever did see.

Is there a more classic lunch combination than tomato soup with grilled cheese? In our take, roasted tomatoes are turned into the most flavourful soup, topped with gooey grilled cheese croutons.

Ingredients for Roasted Tomato Soup

canola or olive oil, for cooking
12-15 plum or Roma tomatoes, halved lengthwise
1 tbsp butter
1 onion, peeled and chopped
2 garlic cloves, crushed
1–2 tsp fresh thyme
1 28-oz can San Marzano-style or diced tomatoes, with their juices
4 cups chicken or vegetable stock
1/2 cup half & half or heavy (whipping) cream
salt and pepper

Ingredients for Grilled Cheese Croutons

6 thick slices crusty bread
butter (optional)
grated aged cheddar or Parmesan cheese, or a combination

Directions for Roasted Tomato Soup with Grilled Cheese Croutons

  1. Preheat the oven to 450˚F. Spread tomatoes out in a single layer on a rimmed baking sheet lined with parchment or foil; drizzle with oil and sprinkle with salt and pepper. Roast for 20–30 min, until soft and starting to turn golden.
  2. In a medium pot set over medium-high, heat another drizzle of oil along with the butter and sauté the onion for 3–4 min, until soft. Add garlic and thyme and cook for 1 min more. Add roasted and canned tomatoes along with chicken stock. Bring to a simmer and let cook for 20 min, or until the tomatoes are very soft.
  3. Remove from the heat, then add cream and purée with a hand-held immersion blender directly in the pot. (Alternatively, carefully transfer to a blender to purée until smooth.) Season with salt and pepper and divide between bowls.
  4. Butter one side of each piece of bread. Sprinkle cheese on the unbuttered side of three slices of bread. Close with the remaining 3 slices, buttered sides facing out (so there is butter on the top and bottom of the sandwich). Place on the baking sheet used in step 1.
  5. Place baking sheet in the top of the oven and toast until top of each grilled cheese is golden, approximately 2-3 min. Flip and toast the other side of grilled cheese for another 2-3 min. (You can turn the oven to broil if you want to speed up this process; just be sure to keep a close eye, as the bread can burn easily.) When finished, allow to cool slightly before cutting into 1-inch squares and floating them on the top of soup.

Serve immediately. Serves 6.

Originally published in ParentsCanada magazine, November 2013. Updated November 2025.