Let Me Tell You About This Soup (And That Grilled Cheese...)

Alright, so picture this: it’s raining cats and dogs outside, you’ve got that kind of cold that seems to crawl right into your bones, and you’re craving something warm, comforting, and, well, a bit nostalgic. That’s exactly when I first whipped up this chunky tomato soup with a grilled cheese twist. My little nephew was over (he’s obsessed with any food that involves cheese), and honestly, regular tomato soup wasn’t going to cut it. So I decided to chunk things up, literally. The addition of a grilled cheese spin wasn’t planned, but you know how inspiration sometimes just kind of whacks you on the head when you’re staring into the fridge. Anyway, let’s just say there were zero leftovers that night, and now this is my rainy-day classic. If you’re into food that feels like a hug in a bowl, you’re in the right place.

Oh, and fair warning – the kitchen might look like a tomato crime scene by the end, but it’s 100% worth it. (If you’re fastidious, maybe lay down a towel or two. Just a thought.)

Why You’ll Love This (Or at Least Why I Do!)

I make this when I need comfort food but I don’t want to mess with too many steps. My family goes a bit bonkers for it because it’s chunky (they say “it eats like a meal”). Also, there’s something really satisfying about dunking grilled cheese bits right into tomato soup. Sometimes I use whatever bread is hanging around—sourdough if I’m feeling fancy, plain white if I’m not. I used to think you had to roast tomatoes from scratch (which is great, don’t get me wrong), but honestly, good-quality canned tomatoes work just fine and save a heap of time. The whole thing is ready in under an hour if you’re not dawdling...unless you get sidetracked mid-recipe like I tend to. And hey, if you're feeling a bit lazy (no judgment), you can even skip the immersion blender step.

What You’ll Need (and What You Can Swap)

Olive oil: 2 tablespoons – Sometimes I’ll use butter instead, especially if I want it richer, but olive oil is what I grab most often.
Yellow onion: 1 medium, chopped (red onion works too, or honestly, I’ve even used shallots in a pinch)
Garlic: 3 cloves, minced. (If peeling garlic is your nemesis, jarred minced garlic gets the job done.)
Canned whole tomatoes: 2 cans (28 oz each). I like San Marzano, but any decent brand will do. My grandmother insisted on Mutti, but honestly, any version works fine.
Vegetable broth: 2 cups. Chicken broth is good if that’s what you got, or even just water with a bouillon cube in a pinch.
Carrot: 1 large, chopped small (I sometimes skip it, but it does add a touch of sweetness.)
Celery: 1 stalk, chopped (optional, but I toss it in if there’s one staring at me from the fridge.)
Dried oregano: 1 tsp. Or Italian seasoning if that’s easier.
Salt & pepper: To taste (I start with a generous pinch and go from there.)
Sugar: 1 teaspoon (optional, but sometimes tomatoes are a bit tangy and need a nudge.)
Heavy cream: Splash, if you want it a bit creamy. Or leave it out, no biggie.
Bread: 4 slices, your choice. Sourdough works well. Rye is a bit wild, but not bad.
Cheese: Enough to make two grilled cheese sandwiches. Cheddar is classic, but I’ve used mozzarella, Gruyère, even a bit of brie once (not sorry).
Butter: For grilling the sandwiches. Margarine works if that’s all that’s in the fridge.

How I Make Chunky Tomato Soup with Grilled Cheese Twist

Heat the olive oil in a big soup pot over medium heat. Add the onion, carrot, and celery (if you’re using it). Cook until softened, about 8 minutes. Stir so nothing sticks—my first few times, I burned the onions, but hey, don’t sweat a bit of color.
Add garlic. Cook for 1 more minute, just until fragrant. I always think it smells amazing at this point.
Now, empty those cans of tomatoes (with juice!) into the pot. Break them up a bit with your spoon. (Sometimes I just squish with my hands right into the pot, which is fun but can get messy. Maybe don’t wear white.)
Pour in the broth, oregano, salt, pepper, and a little sugar if your tomatoes taste super tangy.
Bring to a simmer. Lower the heat and let everything bubble gently, uncovered, for about 25-30 minutes. This is where I usually sneak a taste (or two). Don’t worry if it looks a bit odd at this stage—it always does!
Meanwhile, make your grilled cheese! Butter the bread—don’t skimp. Layer in your cheese of choice. Grill it in a skillet over medium heat until golden and melty. (If you have a sandwich press, great. If not, just press down with a spatula—works a treat.)
Back to the soup: use a potato masher to break up some of the larger tomato pieces for that perfect chunky texture. Or, if you want it smoother, go at it with an immersion blender, but leave some pieces intact. Actually, I find it works better if you don’t blend it completely smooth—let it have some character.
Stir in a splash of cream if you’re feeling fancy. Taste and adjust seasoning.
Cut the grilled cheese sandwiches into cubes (or wedges, if you’re feeling whimsical). Toss a handful right into your soup bowl or serve them on the side for dunking. Up to you.

Stuff I’ve Learned (a.k.a. Notes)

If your soup tastes flat, a squeeze of lemon or a pinch more sugar can wake it up.
Sometimes I use half broth, half water—mostly when I realize mid-cooking that I’m short on broth. It still works fine.
Don’t get too precious about the exact measurements. This recipe’s forgiving—like your favorite old jumper.
Once I tried to double the cream, thinking it’d be extra luscious…well, it just tasted, uh, a bit heavy. Learn form my mistake!

Variations I’ve Messed Around With

Added a handful of fresh basil at the end—delicious, very summery.
Used spicy pepper jack in the grilled cheese once; my mouth was on fire, but my partner loved it.
Tried to make a vegan version with coconut cream and dairy-free cheese. It almost worked, but the coconut flavor was a bit weird for me. Maybe you’ll like it though—give it a bash.
Added roasted red peppers to the soup once, which was fab. Just toss them in with the tomatoes.

What If I Don’t Have That Fancy Equipment?

You really don’t need much: a big pot, a knife, and a cutting board. If you don’t have an immersion blender, a potato masher (or even the bottom of a mug) works in a pinch to chunk up the tomatoes. For grilling cheese, honestly, a regular frying pan does the trick—though if you want those perfect grill marks, a sandwich press is nice (but not essential, despite what my brother-in-law says!).

Chunky Tomato Soup with Grilled Cheese Twist

How To Store It (Not That It’ll Last Long)

Let leftovers cool, then pop them in an airtight container in the fridge. It’ll keep for 3 to 4 days—though honestly, in my house it never lasts more than a day! If you do have extra, heat gently on the stove (soup thickens up, so add a splash of broth or water). Grilled cheese cubes are best fresh, but sometimes I just re-toast them briefly.

Serving Ideas—How We Eat It

I like it straight up, with a big handful of grilled cheese cubes floating on top. My partner insists on a drizzle of chili oil, and my nephew loads his bowl with extra cheddar. Occasionally, I’ll serve it with a quick green salad if I’m pretending to be healthy. And sometimes we eat it standing around the kitchen island, because who says soup has to be formal?

Pro Tips (Learned the Hard Way)

I once tried rushing the simmer time—nope, didn’t get that deep tomato flavor. So, just let it go the full 25-30 minutes if you can.
If you blend it totally smooth, it tastes fine, but the texture’s just not as interesting.
Don’t forget to taste and season as you go; tomatoes can be tricky little things.
And don’t use low-moisture mozzarella for the grilled cheese unless you’re after squeaky, not melty. Learned that one the hard way.

FAQs (Because People Actually Ask These!)

Can I freeze the soup?: Yes, you can! It freezes well for up to a month, though the texture changes a bit. Let it cool before freezing. The grilled cheese doesn’t freeze well, though—make that fresh.
Can I use fresh tomatoes instead of canned?: Sure thing, but you’ll want about 2kg, peeled and chopped. (Check out this guide from Serious Eats if you’ve never peeled tomatoes—it’s actually kind of fun.)
Is there a gluten-free version?: Just use your favorite gluten-free bread for the grilled cheese, and you’re golden. Most of the soup ingredients are already gluten-free.
What’s the best cheese?: I like sharp cheddar, but honestly, it’s a personal thing. I’ve seen people on The Kitchn recommend American cheese for that classic melt. Go with what you love.
Can the soup be made ahead?: Yes! In fact, I think this tastes even better the next day. Just store it in the fridge and reheat gently. Maybe add a splash of broth if it’s thickened up.
Help! My soup is too sour.: A tiny pinch of sugar (or a splash of cream) will fix it. Or just embrace the tang, if you’re into that sort of thing.

Oh, and if you want more fun, homey recipes, I love browsing Smitten Kitchen—Deb’s stories always make me smile.

That’s it—grab a spoon, and let’s call it a meal. Cheers!

Chunky Tomato Soup with Grilled Cheese Twist