This Pioneer Woman Tomato Soup and Grilled Cheese is a classic and comforting recipe, which is made with intensely flavored broiled cherry tomatoes and gooey Gruyère cheese. It’s the ultimate comfort food recipe, ready in about 20 minutes.
Pioneer Woman Tomato Soup and Grilled Cheese Ingredients
Soup:
- 10 ounces cherry tomatoes
- 2 tablespoons tomato paste
- 3 green onions, sliced
- 3 cloves garlic, minced
- 2 tablespoons olive oil
- Kosher salt and freshly ground black pepper
- 1/2 cup heavy cream
- 1 tablespoon balsamic vinegar
- 1 sprig fresh rosemary
- 2 tablespoons pesto
Grilled Cheese:
- 4 slices Jewish rye and pumpernickel swirl bread
- 4 tablespoons pesto
- 8 slices American cheese
- 4 ounces Gruyère, grated
- 1/4 cup mayonnaise
How To Make Pioneer Woman Tomato Soup and Grilled Cheese
- Broil the soup base: Preheat the oven to broil. In a small baking dish, toss the cherry tomatoes, tomato paste, green onions, and garlic with olive oil, salt, and pepper. Place under the broiler for about 6 minutes to lightly char the tomatoes.
- Add cream and finish broiling: Shake the baking dish, then add the heavy cream, balsamic vinegar, and rosemary sprig. Return to the broiler and cook for another 6 to 7 minutes, until the cream has reduced and thickened slightly.
- Blend the soup: Carefully transfer the hot tomato mixture to a blender and puree until smooth. Taste and adjust the seasoning. Divide the soup between two bowls and swirl a tablespoon of pesto into each.
- Build the sandwiches: Lay out the bread slices and spread a tablespoon of pesto on each one. To build each sandwich, layer one slice of bread with 2 slices of American cheese, half the grated Gruyère, and then 2 more slices of American cheese. Top with the second slice of bread.
- Grill the sandwiches: Spread mayonnaise on the outside of each sandwich. Toast in a large skillet over medium heat for 4 to 5 minutes per side, until the bread is golden brown and the cheese is completely melted.
- Serve: Serve the hot grilled cheese sandwiches immediately alongside the warm tomato soup.

Recipe Tips
- Why broil the tomatoes? Broiling the tomatoes at a high heat intensifies their natural sweetness and adds a lovely, slightly smoky flavor to the soup that you can’t get from just simmering.
- What’s the secret to a perfect grilled cheese? Using mayonnaise on the outside of the bread instead of butter is a great trick. It has a higher smoke point, which helps the bread get perfectly golden brown and crispy without burning.
- Can I make the soup ahead of time? Yes, the soup is perfect for making ahead. It can be stored in an airtight container in the refrigerator for up to 4 days and reheated gently on the stove.
- Can I use different bread or cheese? Absolutely. A sturdy sourdough would be a great substitute for the rye swirl. For the cheese, a sharp cheddar or provolone would also be delicious.
What To Serve With Tomato Soup and Grilled Cheese
This classic pairing is a complete meal on its own, but it’s also nice with:
- A few dill pickle spears on the side
- A simple side of potato chips
- A small green salad with a light vinaigrette
How To Store Tomato Soup and Grilled Cheese
- Refrigerate: Store the leftover soup in an airtight container in the refrigerator. The grilled cheese is best enjoyed immediately, but leftovers can be wrapped in foil and refrigerated for up to 2 days. Reheat in a skillet or oven to re-crisp the bread.
Tomato Soup and Grilled Cheese Nutrition Facts
- Serving Size: 1 serving (1 sandwich and 1 bowl of soup)
- Calories: 750 kcal
- Fat: 55g
- Carbohydrates: 40g
- Protein: 25g
Nutrition information is estimated and may vary based on ingredients and cooking methods used.
FAQs
Can I make this vegetarian?
Yes. To make the soup vegetarian, simply ensure your pesto is made without Parmesan (or with a vegetarian-friendly Parmesan) and enjoy the grilled cheese as is.
Why is my soup not smooth?
This soup requires a good blend to become creamy. If you’re using a standard blender, make sure to blend it for at least a full minute. An immersion blender will also work, but may result in a slightly more rustic texture.
Can I make this in a regular pot instead of a cast-iron skillet?
Yes, any non-stick skillet or griddle will work perfectly for making the grilled cheese sandwiches.
Try More Pioneer Woman Recipes:
- Pioneer Woman Sherried Tomato Soup Recipe
- Pioneer Woman Tomato Basil Soup Recipe
- Pioneer Woman Tomato Soup Recipe
Pioneer Woman Tomato Soup and Grilled Cheese Recipe
Description
A quick and flavorful broiled tomato soup served with an extra-cheesy pesto grilled cheese for the ultimate comfort food pairing.
Ingredients
Instructions
- Soup: Broil tomatoes, tomato paste, green onions, and garlic with olive oil for 6 minutes until charred. Add cream, balsamic, and rosemary and broil for another 6-7 minutes.
- Remove the rosemary sprig and carefully blend the hot mixture until smooth. Swirl a tablespoon of pesto into each bowl of soup.
- Grilled Cheese: Spread pesto on all four slices of bread. Layer the cheeses between the slices to make two sandwiches.
- Spread mayonnaise on the outside of the sandwiches.
- Toast in a medium-heat skillet for 4-5 minutes per side until golden and the cheese is melted.
- Serve the sandwiches immediately with the warm soup.
Notes
- u003cliu003eUsing mayonnaise instead of butter on the outside of the grilled cheese is the secret to a perfectly golden, non-burnt crust.u003c/liu003eu003cliu003eBe very careful when blending the hot soup liquid. Do not fill the blender more than halfway and vent the lid.u003c/liu003eu003cliu003eThis is a fantastic recipe for a quick and satisfying lunch or a cozy weeknight dinner.u003c/liu003eu003cliu003eThe combination of American and Gruyère cheese provides both a perfect melt and a delicious, nutty flavor.u003c/liu003e
