Homemade Tomato Soup And Grilled Cheese: The Ultimate Comfort Food Pairing

There are some combinations that are simply perfect. Peanut butter and jelly. Salt and pepper. Macaroni and cheese. But perhaps none is more beloved, more nostalgic, more universally comforting than tomato soup and grilled cheese.

I remember rainy days as a child, pressing my face against the window, watching the world turn gray and wet. And then my mother would appear with a tray—a steaming bowl of creamy tomato soup, golden and fragrant, with a perfectly grilled cheese sandwich sliced diagonally on the side. The world outside might be dreary, but at that moment, everything was warm and right.

That combination has never lost its magic. Even now, as an adult, there are days when nothing else will do. And while canned soup and frozen grilled cheese have their place, nothing compares to making it from scratch—especially when it’s this easy.

This roasted tomato soup is a game-changer. By roasting the tomatoes, onion, and garlic first, you unlock depths of flavor that simmering alone could never achieve. The vegetables caramelize, their natural sugars concentrating into something almost magical. Then a quick whirl in the blender, a swirl of cream, and you have soup that tastes like you spent hours tending it—when really, the oven did most of the work.

And the grilled cheese? We’ll make that perfect too. Crispy, buttery bread giving way to that glorious, stretchy cheese. The ultimate companion to that silky, creamy soup.

Today, I’m sharing everything you need to know to make this classic pairing at home, starting with this incredible roasted tomato soup.

Why This Roasted Tomato Soup Is the Best You’ll Ever Make

Roasting transforms the flavor. The oven concentrates the tomatoes’ natural sweetness and adds a subtle smokiness that you just can’t get from stovetop cooking.

Incredibly creamy without being heavy. A swirl of heavy cream at the end creates that silky texture we all crave, without making the soup feel like a calorie bomb.

Simple, honest ingredients. Tomatoes, onion, garlic, stock, cream, and a few seasonings. That’s it. Nothing complicated, nothing processed.

Better than canned. Once you’ve had homemade roasted tomato soup, you’ll never go back to the canned stuff.

Freezer-friendly. Make a double batch and stash some for those rainy days when only tomato soup will do.

Perfect for using up garden tomatoes. When your garden is overflowing, this is the recipe to make.

Crowd-pleasing. I’ve never met anyone who didn’t love this soup.

Pairs perfectly with grilled cheese. Obviously.

The Complete Ingredient Breakdown

For the Roasted Vegetables:

5-6 medium tomatoes

The star of the show. Use the best tomatoes you can find—they’re the main flavor here. In summer, use garden-ripe tomatoes. In winter, use Roma tomatoes or good-quality greenhouse tomatoes.

Varieties: Roma tomatoes are meaty and perfect for roasting. Beefsteak tomatoes work beautifully too. Cherry tomatoes can be used, but you’ll need more of them.

1 purple onion

Purple onion adds a milder, slightly sweeter flavor than yellow onion. It also adds beautiful color to the roast. If you don’t have purple, yellow or sweet onion work fine.

1-2 heads of garlic

Yes, whole heads of garlic. Roasting transforms garlic from pungent and sharp to sweet, mellow, and almost buttery. Don’t be afraid of the amount—it becomes completely different after roasting.

For Roasting:

Olive oil, for drizzling

Good olive oil helps the vegetables roast and caramelize beautifully.

Salt and pepper, to taste

Essential for bringing out all the flavors.

For the Soup:

½ tablespoon dried oregano or Italian seasoning

Adds that classic Mediterranean flavor that pairs so perfectly with tomatoes.

½ cup vegetable stock

Adds depth and helps create the right consistency. You can also use chicken stock if you’re not vegetarian.

½ cup heavy whipping cream (or more to taste)

This creates that silky, luxurious texture. Start with ½ cup and add more if you like it extra creamy.

For Serving:

Fresh basil leaves (optional)

For garnish and fresh flavor.

Extra drizzle of cream

For that beautiful finish.

Step-by-Step Instructions

Step 1: Preheat and Prep

Preheat your oven to 390°F (200°C). Line a baking sheet with parchment paper for easy cleanup.

Step 2: Prep the Vegetables

Tomatoes: Core the tomatoes and cut them in half. If you’re using larger tomatoes, quarter them so they’re roughly the same size.

Onion: Peel the onion and cut it into thick slices or wedges. You want pieces that will roast well without burning.

Garlic: Slice the top off each head of garlic to expose the cloves. Leave the heads whole—the cloves will roast inside their skins, becoming soft and sweet.

Step 3: Arrange and Season

Place the tomatoes, onion, and garlic heads on the prepared baking sheet. Drizzle generously with olive oil and sprinkle with salt and pepper. Toss gently to coat everything evenly.

Arrange everything in a single layer, giving the vegetables room to roast rather than steam.

Step 4: Roast

Roast at 390°F for 30 minutes, until the tomatoes are softened and starting to caramelize, the onion is tender, and the garlic is soft and fragrant.

The edges of the tomatoes should be slightly charred in spots—that’s where the flavor lives.

Step 5: Cool Slightly

Remove from the oven and let the vegetables cool for about 5-10 minutes, until they’re cool enough to handle.

Step 6: Squeeze the Garlic

Once the garlic is cool enough to handle, squeeze the roasted cloves out of their skins. They should slide right out, soft and buttery. Discard the skins.

Step 7: Blend

Transfer the roasted tomatoes, onion, and garlic to a blender. Add the dried oregano or Italian seasoning and the vegetable stock.

Blend until smooth. Start on low speed and gradually increase to high for the silkiest texture.

Safety tip: Hot liquids expand in the blender and can blow the lid off. Remove the center cap from the blender lid and cover it with a kitchen towel to allow steam to escape while blending.

Step 8: Add the Cream

With the blender running on low, slowly pour in the heavy cream. Blend until the soup is silky smooth and the cream is fully incorporated.

Taste and adjust seasoning—you might want more salt, pepper, or even a pinch of sugar if your tomatoes weren’t super sweet.

Step 9: Serve

Pour the soup into bowls. Garnish with fresh basil leaves and an extra drizzle of cream if desired.

Serve hot with the perfect grilled cheese sandwich.

The Science of Roasted Tomato Soup

Roasting concentrates flavor. Tomatoes are mostly water. When you roast them, that water evaporates, concentrating the natural sugars and creating deeper, more complex flavor. The Maillard reaction (browning) adds savory notes that you just can’t get any other way.

Garlic transforms completely. Raw garlic is sharp and pungent. Roasted garlic becomes sweet, mellow, and almost buttery. It’s a completely different ingredient, and it’s perfect in this soup.

Blending creates emulsion. The natural pectin in tomatoes, combined with the olive oil and cream, creates a stable emulsion that gives the soup its silky texture.

Acid balance. Tomatoes can be quite acidic. If your soup tastes too sharp, a tiny pinch of sugar or a splash more cream can balance it perfectly.

Troubleshooting Common Issues

My Soup Is Too Acidic

Add a pinch of sugar or a little more cream. You can also add a peeled raw potato while blending—it will absorb some acidity (remove it before serving).

My Soup Is Too Thin

Simmer it on the stovetop for 10-15 minutes to reduce and concentrate. Or add a tablespoon of tomato paste to thicken.

My Soup Is Too Thick

Add more vegetable stock or a splash of water until it reaches your desired consistency.

It’s Bland

Add more salt! Seriously, salt is often the missing element. Also check your seasoning—you might need more oregano or even a dash of red pepper flakes.

I Don’t Have a Blender

An immersion blender works perfectly in a large pot. You can also use a food processor, though it won’t get quite as smooth.

My Garlic Tastes Burnt

If your garlic cloves are very small, they may have roasted faster than the tomatoes. Next time, check them at 20 minutes and remove if they’re done.

The Perfect Grilled Cheese: A Quick Guide

While the soup simmers, let’s talk about its perfect partner.

Ingredients:

2 slices good bread (sourdough, white, or Texas toast)

2-3 slices cheese (cheddar, American, Swiss, or a mix)

1-2 tablespoons butter, softened

Instructions:

Step 1: Butter one side of each bread slice. Place butter-side down on a cutting board.

Step 2: Layer the cheese on one slice, then top with the other slice, butter-side up.

Step 3: Heat a skillet over medium heat. Place the sandwich in the pan and cook for 3-4 minutes per side, until golden brown and the cheese is melted.

Step 4: Slice diagonally and serve alongside the soup.

Delicious Soup Variations

Once you’ve mastered the classic, try these variations.

Spicy Roasted Tomato Soup

Add ½ teaspoon red pepper flakes to the vegetables before roasting, or add a chopped jalapeño. The heat is wonderful.

Roasted Red Pepper and Tomato Soup

Add 2 roasted red peppers (jarred or homemade) to the blender along with the tomatoes. The sweetness is incredible.

Basil Tomato Soup

Add a handful of fresh basil leaves to the blender along with the other ingredients. The fresh herb flavor brightens everything.

Coconut Curry Tomato Soup

Replace the heavy cream with coconut milk and add 1 teaspoon curry powder. A completely different but delicious twist.

Creamy Tomato Bisque

Add an extra ¼ cup cream and strain the soup through a fine-mesh sieve for the silkiest, most elegant texture.

Smoky Tomato Soup

Add ½ teaspoon smoked paprika to the blender. The smokiness is wonderful.

Tomato and Roasted Red Pepper Soup with Goat Cheese

Add crumbled goat cheese to each bowl before serving. The tangy cheese is perfect with the sweet tomatoes.

Vegan Tomato Soup

Use plant-based cream or omit the cream entirely and blend in a handful of raw cashews for creaminess.

What to Serve With Tomato Soup

Grilled cheese: The classic. You can’t have one without the other.

Crusty bread: For dipping and sopping.

Grilled cheese croutons: Cut grilled cheese into cubes and float them on top.

Fresh basil: A chiffonade of fresh basil adds color and flavor.

Parmesan cheese: A sprinkle of freshly grated Parmesan is wonderful.

Pesto: Swirl a spoonful of pesto into each bowl.

Croutons: For extra crunch.

A simple salad: With a bright vinaigrette.

Storage and Make-Ahead Tips

Refrigerator: Store in an airtight container in the refrigerator for up to 5 days. The flavor actually improves overnight.

Freezer: This soup freezes beautifully for up to 3 months. Cool completely, then transfer to freezer-safe containers. Thaw in the refrigerator overnight.

Reheating: Reheat gently on the stovetop over medium-low heat, stirring occasionally. You can also microwave individual portions. Add a splash of water or stock if the soup has thickened.

Make-ahead for parties: Roast the vegetables up to 2 days ahead and refrigerate. Blend and add cream just before serving.

Meal prep: Make a double batch and portion into containers for easy lunches all week.

Why This Recipe Deserves a Place in Your Kitchen

This Homemade Tomato Soup represents everything I want in a comfort food recipe. It’s simple enough for a weeknight but impressive enough for company. It transforms humble ingredients into something special. It fills your kitchen with incredible aromas. And paired with a perfect grilled cheese, it’s the ultimate comfort meal.

I’ve made this soup on rainy days when only comfort would do. I’ve made it for sick friends who needed nourishment. I’ve made it for family dinners where it was the star of the show. Every single time, it delivers.

There’s something magical about that first spoonful—the silky texture, the deep tomato flavor, the hint of roasted garlic and sweet onion. It’s soup that nourishes more than just your body; it nourishes your soul.

This recipe has become a staple in my kitchen for good reason. It’s reliable, versatile, and always welcome at the table.

And now it can be that for you too.

So preheat that oven. Halve those tomatoes. Roast that garlic. And get ready to make the most incredible tomato soup of your life.

Your grilled cheese is waiting.

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Have you made this Roasted Tomato Soup? What’s your favorite grilled cheese combination? I’d love to hear about your experience in the comments below!

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