Creamy Tomato Soup with Grilled Cheese “Croutons”

Is there anything more comforting than tomato soup with grilled cheese? It’s the ultimate comfort food duo that takes us straight back to childhood—but this grown-up version kicks things up about ten notches. The soup is velvety smooth with the perfect balance of tangy tomatoes and rich cream, while those adorable grilled cheese “croutons” are basically the best idea anyone’s ever had.

What makes this recipe special is how the crushed red pepper flakes add just the right amount of heat without overwhelming the natural sweetness of the tomatoes. And those grilled cheese croutons? They’re crispy on the outside, gooey on the inside, and the perfect size for dunking into each spoonful of soup. Trust me, you’ll never want to eat tomato soup any other way again.

Ingredients

For the soup:

• 1 tablespoon olive oil
• 1 onion, diced
• 3 garlic cloves, minced
• ¼ teaspoon crushed red pepper flakes
• 1 bay leaf
• 2 (28-ounce) cans whole tomatoes
• ½ cup heavy cream
• 1 tablespoon brown sugar
• ¾ cup low-sodium vegetable broth
• 1 tablespoon chopped fresh parsley leaves, for garnish

For the grilled cheese croutons:

• 1 tablespoon olive oil
• 4 slices white or wheat bread
• 2 tablespoons unsalted butter, softened
• 4 ounces shredded sharp cheddar cheese

Steps

1. Prepare the grilled cheese croutons first. Heat 1 tablespoon olive oil in a grill pan over medium-high heat. Spread ½ tablespoon butter evenly over one side of each bread slice—this ensures perfect golden browning. Turn the slices over and top 2 slices with the shredded cheddar, distributing it evenly but keeping about ¼ inch from the edges to prevent cheese from oozing out during cooking. Place remaining 2 slices of bread on top, buttered sides facing up.
2. Add sandwiches to the preheated pan and grill until the bread turns a deep golden brown and the cheese is completely melted, about 2-3 minutes per side. You’ll know it’s time to flip when you can see the edges of the bread turning golden and the cheese beginning to melt. Let cool for 1 minute before cutting—this prevents the melted cheese from squeezing out when you cut it. Then cut into 1-inch cubes using a sharp knife.
3. For the soup base: Heat 1 tablespoon olive oil in a large stockpot or Dutch oven over medium heat. Add diced onion, minced garlic, crushed red pepper flakes, and bay leaf. Cook, stirring frequently to prevent garlic from burning, until the onion becomes translucent and softened, about 3-5 minutes. You’ll know the onions are ready when they’re soft but not browned.
4. Stir in the canned tomatoes with their juice. Using a potato masher, break down the tomatoes until they’re in smaller, more manageable pieces—but don’t worry about making them completely smooth as you’ll be blending later. Stir in the ½ cup heavy cream and 1 tablespoon brown sugar, which helps balance the acidity of the tomatoes.
5. Bring the mixture to a gentle boil, then immediately reduce heat to low-medium and simmer until the soup has thickened slightly, about 8-10 minutes. You’ll notice it coating the back of a spoon when it’s reached the right consistency. Remove and discard the bay leaf—it’s important not to skip this step as bay leaves remain tough even after cooking.
6. Using an immersion blender, carefully puree the soup until completely smooth, keeping the blender submerged to avoid splattering hot soup. If you don’t have an immersion blender, transfer soup in batches to a regular blender, filling it only halfway each time and removing the center cap to allow steam to escape. Stir in the ¾ cup vegetable broth until heated through, about 2 minutes. Season with salt and pepper to taste, starting with ¼ teaspoon of each and adjusting as needed.
7. Serve the soup immediately in warmed bowls, topping each serving with a generous handful of grilled cheese croutons and a sprinkle of fresh parsley. The croutons will slowly sink into the soup, so serve quickly for the best texture contrast.

Smart Swaps

• Replace heavy cream with coconut milk (1:1 ratio) for a dairy-free version that maintains creaminess
• Substitute white bread with sourdough for the croutons to add a tangy flavor dimension
• Use fire-roasted canned tomatoes instead of regular for a deeper, slightly smoky flavor
• Swap vegetable broth with chicken broth for a richer flavor profile if not keeping vegetarian

Make It Diabetes-Friendly

• Replace brown sugar with 2 teaspoons monk fruit sweetener to reduce carbs by approximately 12g per serving
• Use whole grain bread instead of white for the croutons to lower the glycemic impact and add 2g of fiber per serving
• Substitute half the heavy cream with ¼ cup plain Greek yogurt to reduce fat while maintaining creaminess
• Serve in smaller 1-cup portions paired with a side salad dressed with olive oil and vinegar to slow carbohydrate absorption

Pro Tips

• For extra-smooth soup, strain through a fine-mesh sieve after blending to remove any remaining tomato seeds or skin
• Make the soup base up to 3 days ahead and refrigerate—just add the broth when reheating and make fresh croutons before serving
• For a deeper flavor, roast the canned tomatoes on a baking sheet at 425°F (220°C) for 20 minutes before adding to the soup
• Cut the grilled cheese into different shapes using cookie cutters for a fun presentation, especially when serving to kids