I love comforting meals, and tomato soup and grilled cheese is one of my favorites. 🥣 This is episode 6 of my holiday cooking series. Enjoy this warm and hearty recipe that's perfect for soup season!
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On a sheet pan, add the tomatoes, onion, and garlic. Sprinkle with salt and pepper.
Bake at 425°F for 15 minutes, then broil on high for 3 minutes.
Transfer the roasted mixture to a blender. Add olive oil and fresh basil. Blend on high until well combined.
In a large pot, melt the butter. Stir in the flour to create a paste.
Gradually pour in the chicken broth, stirring continuously. Add the tomato puree blend and mix well.
Let the soup simmer while you prepare the grilled cheese sandwiches.
Stir in the heavy cream and mix until fully incorporated.
Assemble the sandwiches using Italian bread, deli sliced roast beef and ham, and Colby jack cheese.
Cook the sandwiches on a griddle or skillet until the bread is golden and the cheese is melted.
Save some fresh basil for garnishing the soup before serving.
For extra flavor, brush the bread with melted butter before grilling the sandwiches.
Use a high-speed blender for a smoother soup texture.
Can I use canned diced tomatoes instead of whole peeled tomatoes?
Yes, you can use canned diced tomatoes, but the texture may vary slightly.
Can I make this soup vegetarian?
Yes, substitute the chicken broth with vegetable broth and omit the deli meats in the grilled cheese.
Can I freeze the tomato soup?
Yes, the soup can be frozen for up to 3 months. Avoid adding the cream before freezing; stir it in after reheating.
What other cheese can I use for the grilled cheese?
You can use cheddar, mozzarella, or Swiss cheese as alternatives to Colby jack.
How do I prevent the grilled cheese from becoming soggy?
Ensure the skillet is hot enough and cook the sandwiches on medium heat to achieve a crispy texture.
Hi, I’m Jordann! I’m a home cook and content creator passionate about making comforting, flavor-packed meals feel simple and doable. From slow-cooked favorites to indulgent baked goods, I love sharing recipes that bring people together and make everyday cooking feel special. You’ll usually find me in the kitchen testing, tweaking, and filming recipes that are as fun to make as they are to eat—because good food doesn’t have to be complicated to be incredible.
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