Golden grilled cheese paired with creamy tomato soup is the ultimate vegetarian comfort food duo. A family-friendly classic that's warm, satisfying, and perfect for rainy-day lunches.
Heat 1 tbsp olive oil in a medium saucepan over medium heat. Add diced onion and sauté for 3–4 minutes until softened, stirring occasionally to avoid browning.
Add canned crushed tomatoes, vegetable broth, sugar, kosher salt, and ground black pepper. Stir well, bring to a boil, then immediately reduce to a simmer. Simmer uncovered for 12–15 minutes, stirring occasionally.
Turn off heat and use an immersion blender to carefully purée the soup in the pot until smooth. Stir in heavy cream and keep warm on lowest heat, stirring occasionally.
Meanwhile, assemble grilled cheese: Butter one side of each bread slice. Place 4 bread slices, buttered-side down, on a skillet over medium-low heat. Top each with 2 slices of cheddar cheese, then cover with remaining bread slices, buttered side up.
Cook grilled cheese sandwiches for 3–4 minutes per side, pressing gently with a spatula, until bread is deep golden and cheese is melted. Adjust heat as needed to avoid burning.
Transfer sandwiches to a cutting board, let cool briefly, then slice in half. Serve immediately with hot creamy tomato soup.