Easy Homemade Tomato Soup Recipe with Grilled Cheese Croutons

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This easy homemade tomato soup recipe topped with grilled cheese croutons is the perfect comfort food for a cold, winter day. This post has been sponsored but all opinions are my own.

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When I was asked to create my favorite comfort food recipe for a project with Cabot cheese, I knew I wanted to make some type of grilled cheese sandwich…all warm and gooey! Of course, you can’t have a grilled cheese sandwich without a tasty bowl of tomato soup. The two just go together like peanut butter and jelly, right? When I was young, my soup came from a can and my grilled cheese was white bread and processed orange cheeze slices. Not exactly the healthiest choice but I do remember it tasting delicious. Now that I’m all grown up, I decided to make this easy homemade tomato soup recipe and instead of crackers, add a handful of grilled cheese croutons to the top of the bowl. It was a delicious combination and the perfect meal for a cold, winter day!

Easy Homemade Tomato Soup Recipe with Grilled Cheese Croutons

Growing up an hour outside of New York City meant a fairly robust Jewish community and a wonderful selection of delis with warm, rye bread. Rye and Sourdough are my two favorite types of bread and I think the strong flavor really makes a sharp cheddar just stand out. You will want to make the grilled cheese sandwich first and allow it to cool while you make the soup. That way, the cheese firms back up again and doesn’t ooze everywhere when you cut the sandwich into tiny crouton size bites. I used the Cabot Farmhouse Reserve and it was delicious.

Easy Homemade Tomato Soup and Grilled Cheese Croutons

Easy Homemade Tomato Soup Recipe

with Grilled Cheese Croutons

Yield: 4 to 6 servings

Easy Homemade Tomato Soup Recipe with Grilled Cheese Croutons

Easy Homemade Tomato Soup Recipe with Grilled Cheese Croutons

This easy homemade tomato soup recipe is topped with grilled cheese 'croutons' for an easy variation of your favorite comfort food.

Prep Time 10 minutes
Cook Time 40 minutes
Total Time 50 minutes


  • 4 slices rye bread
  • 4 TBSP butter, softened
  • 4 ounces Cabot sharp cheddar cheese, sliced
  • 3 to 4 tablespoons olive oil
  • 1 small onion, diced
  • 3 garlic cloves, minced
  • 4 (14 ounce) cans diced tomatoes
  • 1/2 to 3/4 cups heavy cream
  • 1 cup chicken or vegetable broth
  • salt and pepper to taste
  • 1 tablespoon chopped fresh parsley leaves, for garnish


  2. Heat a skillet over medium heat until warm. Butter one side of each slice of bread. Place 2 slices butter side down on the skillet. Layer in slices of Cabot cheddar. Lay the other slices of bread on top of the cheese, butter side up. Grill until bottom is starting to brown. Flip the sandwiches and grill the other side until golden brown. Turn off heat and remove sandwiches from pan and let cool. Cut into small squares with a sharp knife.
  4. Heat oil in a large pot over medium heat.
  5. Add the onion and garlic and saute 3 to 4 minutes.
  6. Add the canned tomatoes (do not drain!) and the stock
  7. Bring contents to a simmer. Cover and cook 20 minutes.
  8. Remove from heat and let cool slightly
  9. Using an immersion blender, puree soup until smooth
  10. Return to heat and add 1/ cup heavy cream. Stir to combine. Add a bit more if it is too thick.
  11. Season with salt and pepper
  12. TO SERVE:
  13. Place soup in the bowl. Top with a few grilled cheese 'croutons'. Sprinkle with fresh parsley and a tad bit more black pepper.


Looking for more comfort food recipes?

Check out this delicious Shepherd’s Pie Recipe with Leeks

 Easy Shepherd’s Pie Recipe with Leeks




  1. LOVE this! Looks so perfect for chilly winter nights!

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