Creamy Roasted Tomato Soup with Grilled Cheese Croutons

Written by Dietitian & Mom: Elis Halenko

A dreamy, cozy classic—with a wholesome, modern upgrade.

Let’s be real: nothing says comfort quite like a steaming bowl of tomato soup paired with grilled cheese. But this isn’t the canned tomato soup of your childhood—this is the elevated version that warms you from the inside out, is packed with roasted vegetables, and still delivers that nostalgic grilled cheese hit your kids (and you!) crave.

Inspired by @carolinagelen and adapted based on what I had on hand (because real life = using up what’s in the fridge), this creamy roasted tomato soup is hearty, wholesome, and seriously dreamy. And those grilled cheese croutons? Say less. 🧀

Why You’ll Love This Soup

Roasting adds deep, rich flavor
Packs in hidden veggies (your kids won’t even notice!)
Made with simple pantry + fridge staples
Grilled cheese croutons = the ultimate comfort food moment

Freezer-friendly and toddler-approved

Ingredients (Serves 4)

For the Soup:

8–9 vine-ripe tomatoes, halved
1/2 butternut squash, peeled and chopped
2 small yellow onions, quartered
1 large red bell pepper, deseeded and chopped
5–6 cloves garlic
1–2 tbsp olive oil
Salt & pepper to taste
1/2 cup vegetable stock (or more if needed)
A few leaves of fresh basil
Optional: extra garlic, a splash of cream, or chili flakes

For the Grilled Cheese Croutons:

4 slices of whole grain or sourdough bread
4 slices of cheddar or mozzarella cheese
1–2 tbsp butter

Instructions:

1. Roast the Vegetables

Preheat oven to 400°F (200°C). On a large baking sheet, place halved tomatoes, butternut squash cubes, onions, red pepper, and garlic cloves. Drizzle with olive oil and season with salt + pepper. Roast for 20–25 minutes until veggies are soft and caramelized.

2. Blend the Soup

Transfer the roasted veggies to a blender. Add vegetable stock and fresh basil. Blend on high until smooth. Taste and season with extra salt, garlic, or herbs if needed.

3. Simmer

Pour the soup back into a large pot. Simmer on medium-low heat for about 20 minutes, allowing it to thicken and the flavors to deepen. Stir occasionally.

4. Make the Grilled Cheese Croutons

While the soup simmers, make your grilled cheese sandwiches. Butter one side of each slice of bread, sandwich the cheese inside, and grill until golden brown. Let cool slightly, then cut into bite-sized cubes.

5. Serve

Ladle soup into bowls, top with grilled cheese croutons, and serve immediately while the croutons are still crispy!

Family Tips & Real Life Swaps

Got picky eaters? The roasted red pepper + butternut squash adds natural sweetness and creaminess without needing dairy.
Swap the squash for a couple of carrots or sweet potato if that’s what you have.
Want more protein? Stir in a can of white beans or top with Greek yogurt instead of cream.
Freeze leftover soup (without croutons) in individual portions for easy lunches.

From My Kitchen to Yours

This is the soup I dream about on cold afternoons—the kind of dish that brings everyone to the table, makes the kitchen smell incredible, and checks both the “comfort” and “nutrient-rich” boxes. And yes, the grilled cheese croutons are totally non-negotiable.

Ella absolutely loved dipping and munching these, and it reminded me how classic dishes don’t have to be boring—they just need a little love and inspiration.

📸 Cook With Me!

If you try this dreamy tomato soup, tag me @thefoodstylistrd. I’d love to see your version—grilled cheese on the side or croutons on top?