1. Preheat oven to 425 degrees.

2. In a large dutch oven or an oven-safe pot, combine canned whole tomatoes, onions, garlic, oil, Italian seasoning, salt, and black pepper. Bake that, uncovered for about 30 minutes.

2. Blend the mixture together with an immersion blender or transfer the roasted mixture to a blender and blend until smooth. If using a blender, transfer it back into the dutch oven.

3. To the soup, add the cream and chicken broth and stir to combine. Add in more or less chicken broth depending on the consistency you like. Cook that over low heat for 5 minutes. Optionally add in more salt and pepper to taste. 

4. To make the grilled cheese, first combine the cheeses; 1 cup freshly shredded cheddar cheese, and 1 cup freshly shredded Monterey jack cheese. Now, take 8 slices of thick-cut bread, and spread 2 Tbsp. mayo over one side of each slice. To a pan over medium heat, place a slice of bread (mayo side down) and add on about 1/4 of the cheese mixture to the slice. Let the cheese melt for about 2 minutes, then top with another slice of bread, flip and continue to cook for another 2 minutes. Repeat until you have 4 sandwiches.

4. Divide the soup among 8 bowls. Serve with grilled cheese and enjoy!