Few meals are as comforting as a crispy grilled cheese sandwich served alongside a warm bowl of homemade tomato soup. Golden, buttery bread, melted cheese, and rich, creamy tomato soup make this classic combination perfect for cool fall afternoons, easy weeknight dinners, or a cozy weekend lunch.
This recipe keeps things simple while building plenty of flavor with roasted tomatoes, garlic, herbs, and a blend of cheeses for the grilled cheese.
Homemade Creamy Tomato Soup
Roasting the tomatoes, onion, and garlic before blending gives this soup a deeper, richer flavor while still keeping the recipe easy to prepare.
Ingredients
For the Tomato Soup:
- 2 lbs ripe Roma or plum tomatoes, halved
- 1 medium yellow onion, roughly chopped
- 5 cloves garlic
- 2 tbsp olive oil
- 1 can (28 oz) whole peeled tomatoes
- 2 cups vegetable or chicken broth
- 1 tbsp tomato paste
- 1 tsp dried oregano
- ½ tsp dried thyme
- ½ tsp red pepper flakes, optional
- ½ cup heavy cream
- 1 tsp sugar, optional
- Salt and freshly ground black pepper, to taste
- Fresh basil, for serving
For the Grilled Cheese:
- 8 slices sourdough or your favorite sandwich bread
- 4 tbsp softened butter
- 1 cup shredded sharp cheddar cheese
- 1 cup shredded mozzarella or Gruyère cheese
Instructions
1. Roast the Tomatoes
Preheat your oven to 425°F (220°C).
Arrange the fresh tomatoes, onion, and garlic on a baking sheet. Drizzle with olive oil and season with salt and black pepper.
Roast for 30–35 minutes, or until the tomatoes are soft and beginning to caramelize around the edges.
2. Build the Soup
Transfer the roasted tomatoes, onion, and garlic to a large pot.
Add the canned tomatoes, broth, tomato paste, oregano, thyme, and optional red pepper flakes.
Bring to a gentle simmer and cook for approximately 15–20 minutes.
3. Blend Until Smooth
Remove the pot from the heat and carefully blend the soup directly in the pot using an immersion blender.
Continue blending until smooth and creamy.
4. Finish the Tomato Soup
Return the soup to low heat and stir in the heavy cream.
Taste and season with additional salt and black pepper as needed. If your tomatoes are particularly acidic, add a small amount of sugar to balance the flavor.
Keep the soup warm over low heat while preparing the sandwiches.
Homemade Grilled Cheese
5. Assemble the Sandwiches
Spread softened butter over one side of each slice of bread.
Place the bread butter-side down and divide the cheddar and mozzarella or Gruyère between four slices. Top with the remaining bread, keeping the buttered sides facing outward.
6. Grill Low & Slow
Heat a skillet or griddle over medium-low heat.
Add the sandwiches and cook for approximately 3–4 minutes per side, gently pressing them with a spatula.
Cooking over moderate heat gives the cheese enough time to melt before the bread becomes too dark.
7. Serve
Slice each grilled cheese in half and serve immediately alongside a bowl of warm tomato soup.
Finish the soup with fresh basil, freshly cracked black pepper, a drizzle of cream, or grated Parmesan if desired.
Why This Recipe Works
Roasting the fresh tomatoes, onion, and garlic concentrates their flavors and adds a subtle caramelized sweetness before they are incorporated into the soup. Canned tomatoes provide consistency and additional tomato flavor, while cream softens the acidity and creates a smooth finish.
For the grilled cheese, combining sharp cheddar with a good melting cheese like mozzarella or Gruyère provides both flavor and that signature cheese pull. Cooking the sandwich over medium-low heat gives the cheese time to melt while creating an evenly crisp, golden exterior.
Tips for the Best Grilled Cheese and Tomato Soup
- Roast the tomatoes until lightly caramelized for a deeper soup flavor.
- Use an immersion blender to blend the soup directly in the pot with less cleanup.
- Choose sturdy bread such as sourdough that can develop a crisp exterior without becoming too soft.
- Shred your cheese to help it melt more quickly and evenly.
- Keep the skillet at medium-low heat so the bread doesn't burn before the cheese melts.
- Customize your grilled cheese with caramelized onions, pesto, bacon, or thinly sliced tomatoes.
- Make the soup ahead and reheat it for a quick fall lunch or dinner.
Explore our selection of high-quality immersion blenders to turn roasted tomatoes, garlic, and herbs into smooth, creamy homemade tomato soup directly in the pot.
