Old Fashioned Grilled Cheese and Tomato Soup

Sometimes you need some good old fashioned comfort food–nothing fancy or too difficult. Not sure what fits that description more than grilled cheese and tomato soup which my sister and I made last week on a cold fall night. This recipe is pretty simple and doesn’t require a ton of ingredients. I do recommend you check out my recipe for adult grilled cheese because that takes it to a whole other level. But this is just good home cookin!

Tomato Soup Ingredients:

  • 2 cans San Marzano Tomatoes
  • 6 or 7 roasted garlic cloves (Cut off the top of the bulb, roast in toaster oven with oil inside tin foil for at least 45 minutes at 375)
  • 1/2 of sweet onion
  • Fresh fennel (optional but it’s great flavor. You could also substitute leeks)
  • Carrot (I only had a white one on hand)
  • 1 TBSP butter
  • Fresh dill
  • Fresh Thyme
  • Bay leaf
  • Fresh chives (optional for topping)

Grilled Cheese Ingredients:

  • Bread- critical component. Don’t overlook finding the perfect bread
  • American Cheese
  • Fontina Cheese – this is a good melty italian cheese. You can opt to go the more traditional route for cheddar but this is what screamed to me in the grocery store
  • Spinach- optional
  • Cast Iron Pan


Put about 1 TBSP of butter and some olive oil in a pan. Add onions, fennel and carrots and saute for a few minutes.

Then season with salt, pepper and add herbs. I like to remove the thyme and bay leaf so I tied it in a bundle. But the dill should stay in there! 

These are the best canned tomatoes… for the record. 

Pour in the tomatoes and bring to a boil. Use a wooden spoon to break up the tomatoes a bit. Then reduce to a simmer and let cook for a few. Let’s prep the sandwiches… 

Add the garlic when it’s ready. This could have been cooked more but it was still delish!

Assembly line… if you are using spinach make sure to place it in between the cheese layers.

When the assembly line is complete, puree your sauce to your liking. I left it just a tiny bit chunky. Then let the soup simmer for a few more minutes. 

Nom nom nom nom. How good does that look?

Butter your bread.

Get your cast iron skillet hot and put in sandwiches. Make sure to press down on them. I also put a lid on them for a few minutes to get the cheese nice and melty. 

Top the soup with some fresh chopped chives and fresh cracked black pepper. 

I don’t think it get’s any better… Nosh and Mangia… 

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