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Preheat your oven to 425 degrees.
Slice 8 - 9 ripe tomatoes into quarters and place in a large Dutch oven. Dice your onion into quarters and place in the Dutch oven on top of your tomato's.
Slice the top of your garlic head off, revealing the cloves inside and the skin still on the garlic, and place in the middle of the Dutch oven. Drizzle with olive oil and sprinkle with the salt and Italian seasoning.
Place the lid on the Dutch oven and put the whole thig into the oven on the lower rack. Bake for 1 hour.
Take the Dutch oven out and remove the lid, releasing the steam. It will be HOT.
Carefully squeeze the roasted garlic cloves out of the bulb and let them fall straight into the vegetables. Discard the outer portion of the garlic.
Pour in the chicken broth, and with your immersion blender, give everything a rough blend so the tomatoes and onions are broken up.
Pour in the half and half and oregano, using your immersion blender again, blend everything well until you have a smooth soup.
Serve warm with a side of grilled cheese, topped with sourdough crutons, or inside of a bread bowl! :)