There’s nothing cozier than a warm bowl of creamy tomato soup and a golden, melty grilled cheese sandwich.
It’s the kind of meal that feels like a hug. This is my go-to on chilly evenings or when I need something fast, comforting, and satisfying.
It’s simple but full of flavor, and roasting the tomatoes brings out that deep, rich taste you just can’t get from the can alone.
Why I Love This Recipe
This recipe takes a classic and gives it a little upgrade, without making it complicated. Roasting the tomatoes and garlic brings out this naturally sweet, deep flavor that tastes homemade but doesn’t take all day. It’s also a great one for sharing — it feels a little special but is totally weeknight-friendly.
- Roasting the tomatoes makes everything taste better — sweet, deep, and caramelized
- You only need simple ingredients, but it tastes like something from a fancy café
- It’s a full meal with the grilled cheese and soup combo
- Easy to make ahead or freeze
- Total comfort food, perfect for chilly weather
Servings: 4
Prep Time: 15 minutes
Cook Time: 45 minutes
Total Time: 1 hour
What You’ll Need
For the Tomato Soup:
- 2 lbs roma tomatoes, halved
- 1 onion, peeled and quartered
- 6 garlic cloves, peeled
- 2 tbsp olive oil
- 1 tsp salt
- ½ tsp black pepper
- 1 tsp dried basil
- ½ tsp crushed red pepper flakes (optional)
- 2 cups vegetable broth
- ½ cup heavy cream
For the Grilled Cheese:
- 8 slices sourdough or white bread
- 2 cups shredded sharp cheddar cheese
- 4 tbsp butter, softened
Pro Tips
- Roast the garlic with the tomatoes — it gets sweet and mellow, not sharp
- Blend the soup while it’s still warm but not piping hot — safer and smoother
- Use day-old bread for grilled cheese; it crisps up better
- Add cream slowly while stirring so it blends evenly and doesn’t separate
- For extra flavor, add a splash of balsamic vinegar to the soup before blending
Tools Required
- Sheet pan
- Blender or immersion blender
- Large pot
- Ladle
- Skillet or griddle
- Spatula
- Cutting board and knife
Substitutions and Variations
- Use canned whole tomatoes if fresh aren’t in season (roast them anyway!)
- Swap heavy cream with coconut milk for a dairy-free version
- Use mozzarella or a cheese blend for grilled cheese
- Add a pinch of sugar if your tomatoes taste too acidic
- Try rye or multigrain bread for the sandwich
Make Ahead Tips
- Roast the tomatoes, garlic, and onions the day before. Store in the fridge.
- The soup can be made ahead and stored for 3 days or frozen up to 2 months.
- Grilled cheese is best fresh, but you can prep the buttered bread slices ahead of time.
Cooking Steps
Step 1: Roast Tomatoes, Onion, and Garlic
Place 2 lbs halved roma tomatoes, 1 quartered onion, and 6 peeled garlic cloves on a sheet pan. Drizzle with 2 tbsp olive oil, then sprinkle with 1 tsp salt, ½ tsp black pepper, 1 tsp dried basil, and ½ tsp crushed red pepper flakes (optional). Toss everything to coat, then spread in a single layer. Roast at 425°F for 30 minutes.
Step 2: Blend the Roasted Veggies
Once cool enough to handle, transfer all roasted tomatoes, onion, and garlic into a blender. Add 2 cups vegetable broth. Blend until smooth and creamy.
Step 3: Simmer the Soup
Pour the blended soup into a large pot. Heat over medium heat until bubbling. Stir in ½ cup heavy cream and reduce heat to low. Simmer for 10 minutes, stirring occasionally.
Step 4: Make the Grilled Cheese
Butter one side of each slice of bread (8 slices total). Place 4 slices butter-side down in a skillet. Add ½ cup shredded cheddar on each slice. Top with remaining slices, butter-side up. Cook on medium heat until golden brown on both sides and cheese is melted, about 3–4 minutes per side.
Step 5: Serve and Enjoy
Ladle soup into bowls, drizzle with extra cream if you like, and serve with grilled cheese on the side or dipped right in.
Leftovers and Storage
- Store leftover soup in an airtight container in the fridge for up to 3 days.
- Freeze soup for up to 2 months (leave out cream until reheating if freezing).
- Reheat soup gently on the stove.
- Grilled cheese can be reheated in a skillet to crisp back up, but best eaten fresh.
Macros (Per Serving, including 1 grilled cheese + soup)
Calories: 520
Protein: 16g
Fat: 32g
Carbs: 42g
Fiber: 6g
Sugar: 12g
Why This Recipe Works (Quick Science)
Roasting tomatoes evaporates water and concentrates natural sugars, giving the soup a deeper, sweeter flavor. Roasting garlic takes away its harshness and adds warmth. Blending the soup while warm helps emulsify the olive oil and cream into a velvety texture. Grilled cheese gets its golden crust from butter and heat, and shredded cheese melts more evenly than slices.
Common Mistakes
- Skipping the roast: raw tomatoes don’t give the same flavor punch.
- Blending too hot: can cause pressure buildup — let it cool a bit first.
- Using too much broth: it thins out the soup too much. Stick to 2 cups.
- Overcooking grilled cheese: medium heat is key for melty insides and golden outsides.
- Not seasoning: taste the soup before serving and adjust salt if needed.
What to Serve With
- Side salad with balsamic vinaigrette
- Roasted veggies or crispy potato wedges
- Crackers or garlic bread
- Chopped fresh herbs or parmesan for topping
FAQ
Can I use canned tomatoes?
Yes! Use whole peeled tomatoes and roast them like fresh.
Can I make this dairy-free?
Yep — use coconut milk or oat cream, and a vegan cheese/butter.
Do I need a blender?
An immersion blender works great too, just blend right in the pot.
Can I freeze this soup?
Totally! Just leave out the cream before freezing and add it when reheating.
Final Thoughts
This roasted creamy tomato soup and grilled cheese is one of those feel-good meals that always hits the spot. It’s simple, cozy, and packed with flavor thanks to the roasting step. Try it on your next soup-and-sandwich night, then leave a comment to let me know how it turned out or if you have any questions.