Tomato Soup with Grilled Cheese

A white bowl of creamy orange-red tomato soup with a spoon, served with a grilled cheese sandwich.

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This Tomato Soup with Grilled Cheese is the perfect comfort food pairing. Smooth, savory soup meets crispy, melty sandwich in this easy and nostalgic recipe.

Prep Time10

Cook Time25

Total Time35

Course: Main Course

Cuisine: American

Keyword: Easy comfort food, grilled cheese, homemade soup and sandwich, tomato soup

Servings: servings

Calories: 508kcal

Author: Chef Jenn

Ingredients

For the Tomato Soup:

2 tablespoons olive oil
1 small onion chopped
2 cloves garlic minced
1 tablespoon tomato paste
28 ounces whole peeled tomatoes
2 cups vegetable broth
1 teaspoon sugar
½ teaspoon dried oregano
salt to taste
ground black pepper to taste
¼ cup heavy cream optional

For the Grilled Cheese:

4 slices sourdough or country-style bread
4 slices sharp cheddar cheese
2 tablespoons butter softened

Instructions

Heat olive oil in a medium soup pot over medium heat. Add the chopped onion and cook until softened, about 5 minutes. Stir in the garlic and tomato paste, and cook for 1 minute to bring out the flavor.
Pour in the canned tomatoes (with their juice) and vegetable broth. Break up the tomatoes with a spoon. Stir in the sugar, oregano, salt, and black pepper.
Bring the mixture to a simmer and let it cook uncovered for 20 minutes, stirring occasionally, until the flavors deepen.
Use an immersion blender to puree the soup directly in the pot, or transfer it carefully in batches to a countertop blender and blend until smooth.
Stir in the heavy cream if using, then taste and adjust the seasoning with salt and pepper. Keep warm while you prepare the sandwiches.
Butter one side of each slice of bread. Layer the cheddar cheese between two slices, buttered sides out.
Grill the sandwiches in a skillet over medium heat for 3–4 minutes per side, or until the bread is golden brown and the cheese is melted.
Slice the grilled cheese sandwiches in half and serve hot alongside bowls of tomato soup.

Notes

Chef Jenn’s Tips

For even more flavor, roast the tomatoes before adding them to the soup.
Don’t skip the sugar—it helps balance the acidity of the tomatoes.
Try swapping cheddar for fontina, mozzarella, or pepper jack for different grilled cheese flavor combos.
Use an immersion blender for the easiest cleanup, or leave the soup slightly chunky if you prefer more texture.

Nutrition