This cozy tomato soup paired with golden, melty grilled cheese sandwiches is the ultimate comfort food combo. Perfect for a quick weeknight dinner or nostalgic lunch, this recipe features a rich, creamy soup made from pantry staples and crisp sandwiches oozing with gooey cheese. It’s a warm hug in a bowl, ready in under 40 minutes.
Warm the olive oil in a medium pot over medium heat. Add the chopped onion and cook for about 5 minutes, until softened. Stir in the garlic and tomato paste, cooking for another minute.
Add the canned tomatoes with their juice and the vegetable broth. Use a spoon to roughly break apart the tomatoes. Mix in the sugar, oregano, salt, and pepper.
Bring the soup to a simmer. Cook uncovered for about 20 minutes, stirring now and then so nothing sticks to the bottom.
Blend it smooth with an immersion blender once the soup has reduced a bit, or carefully transfer it in batches to a blender. Stir in the heavy cream if you're using it. Taste and adjust seasoning if needed. Keep the soup warm while you grill the sandwiches.
Spread butter on one side of each slice of bread. Layer the cheddar between two slices with the buttered sides facing out.
Place the sandwiches in a skillet over medium heat. Grill for 3–4 minutes per side until the bread is golden and crisp and the cheese has melted.
Cut the sandwiches in half and serve hot with a bowl of the tomato soup.
Notes
Chef Jenn's Tips
Roasting the tomatoes before adding them gives the soup even more depth.
A bit of sugar cuts the sharpness of the tomatoes—don’t skip it.
Want to switch it up? Use mozzarella, fontina, or pepper jack in your grilled cheese.
An immersion blender makes cleanup simple and keeps everything in one pot.
Nutritional information for this recipe is provided as a courtesy and is calculated based on available online ingredient information. It is only an approximate value. The accuracy of the nutritional information for any recipe on this site cannot be guaranteed.