Butter Tomato Soup with the Creamiest Grilled Cheese and Balsamic Roasted Veggies

We all need this classic in our life. Sometimes you just need a good, big bowl of tomato soup and a crispy, ooey, gooey grilled cheese to dunk on into it. Its a must. My inspiration for this recipe came from The Flourishing Foodie and her Butter Onion Tomato Soup with Pasta and Parmesan and the fact of making a butter tomato soup just blew my mind and I was hooked on the idea. I just had to see what this was all about! And oh boy, it is SO worth it! I went down a more traditional route with the soup to make it a more classic tomato and basil combo, and I just can’t get over the depth and flavor of this soup! We’ve had it like 4 times in the past couple weeks and there is no shame at all.

You just can’t have a bowl of tomato soup without having a grilled cheese to go along with it. Thats just like having macaroni with no cheese – it just isn’t right! A grilled cheese needs to have the perfect, golden-brown crust that cracks open to reveal a cheesy, gooey center ready to be dunked into a perfect bowl of tomato soup. My secret ingredient to my ultimate grilled cheese sandwich is a nice smear of cream cheese on the bread before you top it off with the classic cheddar cheese. Shhhh don’t tell anyone. Its that good.

The addition of the balsamic roasted veggies helps make it a more rounded meal to me. It just completes the tomato soup and grilled cheese combo! Plus, what a great way to sneak in some more veggies for your kids! I like the combination of butternut squash, kale and cauliflower, but feel free to use whatever you have on hand! Broccoli, carrots, spinach, sweet potatoes any of it will do. What I love about all of these elements is that you can fondue-style it. I mean if you really think about it, dipping a grilled cheese sandwich into your tomato soup is almost like fondue – a tomato soup fondue. Dip those veggies just the same! Or stir them all into the velvety soup to get complete coverage and add some more depth to your soup.

This meal deal is the perfect weeknight, weekend, make ahead or re-heat leftovers kind of deal. You could even let the soup sit all day in the slow cooker so that all you have to do when you get home is roast some veggies and crisp up your grilled cheese! I love making this and then my husband and I treat ourselves to the leftovers the next couple nights. Are we eating too many grilled cheeses? Don’t even answer that.



Butter Tomato Soup with the Creamiest Grilled Cheese and Balsamic Roasted Veggies

Serves 4 


For the soup:

  • 1 – 28oz can diced tomatoes
  • 1 – 32oz carton vegetable stock
  • 1 medium onion, roughly chopped
  • 1/2 stick (4 tablespoons) butter
  • 2 tablespoons tomato paste
  • 1 teaspoon dried basil
  • 1/2 teaspoon salt, plus more to taste
  • 1/4 teaspoon ground black pepper

For the grilled cheese:

  • 1 loaf sliced sourdough bread
  • 1/2 stick (4 tablespoons) butter, softened
  • 8 oz sharp cheddar cheese
  • 4 oz cream cheese, softened
  • Garlic salt to taste

For the veggies:

  • 3 cups chopped butternut squash
  • 2 cups cauliflower florets
  • 2 cups chopped kale
  • 1 1/2 tablespoons olive oil
  • 1 tablespoon balsamic vinegar
  • Salt and Pepper



  1. In a large pot, bring the diced tomatoes, vegetable stock, 1/2 stick of butter, onion, and tomato paste to a low boil. Reduce the heat to low, cover with a lid and let cook for 45 minutes to an hour. Using either a blender, food processor or an immersion blender, blend the soup mixture until smooth. Return the soup to the original pot (not applicable if using an immersion blender) and stir in the basil, salt and pepper. Taste the soup and add more seasoning as needed. Keep warm until ready to serve.
  2. When the soup is in the last 15 minutes of cooking, preheat your oven to 400 degrees. Toss the veggies with the olive oil, balsamic vinegar and salt and pepper to taste. Spread them on a baking sheet in an even layer and bake for 15 minutes or until the veggies are soft and slightly caramelized.
  3. Using two slices of bread for each grilled cheese, spread the remaining softened butter on the outsides of each slice of bread being used for the grilled cheese. Dividing the ingredients evenly amongst the number of sandwiches, continue to spread the cream cheese on the inside of one slice of bread per sandwich. Layer the cheddar cheese on top of the cream cheese and lightly sprinkle with garlic salt. Top the cheddar cheese with the second piece of buttered bread.
  4. Preheat a non-stick skillet over high heat and cook the grilled cheese sandwiches buttered side down until golden-brown and crispy on both sides and the cheese is melted, flipping only once.
  5. Serve the tomato soup with the roasted veggies either on the side or on top of the soup, and the grilled cheese sliced and ready to dunk. Enjoy!