Creamy Tomato Basil Soup with Grilled Cheese

Heat the butter and olive oil in a large Dutch oven or soup pot over medium heat. Add the diced onion and cook for about 5 minutes until softened. Stir in the minced garlic and cook for another minute until fragrant.

Add the canned tomatoes with their juices, chicken broth, sugar (if using), salt, pepper, and oregano. Break up the tomatoes with a spoon and bring the soup to a gentle boil. Reduce the heat and simmer uncovered for 20 minutes, allowing the flavors to blend together.

Use an immersion blender to puree the soup until smooth, or carefully transfer it to a blender in batches. Return the soup to low heat and stir in the heavy cream, fresh basil, and Parmesan cheese if using. Simmer for another 2–3 minutes without boiling.

Butter one side of each bread slice. Place four slices butter-side down in a skillet over medium heat. Add two slices of cheddar cheese to each sandwich and top with the remaining bread, butter-side up. Cook for 3–4 minutes per side until golden brown and the cheese is fully melted.

Ladle the hot tomato basil soup into bowls. Slice the grilled cheese sandwiches in half and serve alongside or dip them directly into the soup for the ultimate comfort meal. Garnish with additional basil leaves, cracked black pepper, or grated Parmesan if desired.