Homemade tomato soup is so easy (and so much tastier than store-bought) that it feels silly not to make it yourself. There’s something about the sweetness of gently-softened onions and garlic, plus a little splash of wine and cream, that just turns canned tomatoes into the most delightful pick-me-up on a cold day. And the sandwiches are just perfect— gooey and crunchy at the same time.

Homemade Tomato Soup with Grilled Cheese
Serves: 4
Prep time: 30 minutes
For Dietary Restrictions
Gluten free: Use gluten-free bread
Dairy free: Use olive oil instead of butter; omit cream (soup); use a plant-based butter and dairy-free cheese (sandwiches)
Kids Can Help
open the cans, butter the bread, add cheese slices
Ingredients
For the soup:
2 28 oz cans diced tomatoes
1 onion
6 cloves of garlic
1 Tbsp olive oil
1 tsp salt
1 cup chicken broth
¾ cup heavy cream
splash of white wine, vermouth, or cream sherry (optional)
For the sandwiches:
8 slices of whole grain bread
8 slices of cheddar cheese
½ stick butter, softened
Tools
Cutting board
Chef knife
Large soup pot with a lid
Can opener
Long wooden spoon or spatula
Skillet or baking sheet
Blender or immersion blender, or you can eat this soup without blending if you like it chunky. Just make sure to mince the garlic and onion instead of slicing them!
Directions
Step 1
Peel and slice garlic and onion.
Step 2
In a large soup pot, heat olive oil over medium-low heat. Add garlic and onion and cook until soft, stirring occasionally (reduce heat if they start to brown).
Step 3
Add tomatoes with their juice, chicken broth, and salt. Bring to a simmer and cover. Allow to simmer while you do step 4.
Step 4
While the soup is simmering, make your sandwiches. You have two options:
Stovetop (tastier!): Heat a cast-iron or other non-stick skillet on medium heat. Butter one side of 2 slices of bread and lay in the heated skillet buttered-side down. Lay 1 slice of cheese on each slice of bread. Cover with lid or tinfoil; lower heat. Toast for a minute or two until the cheese is melted, checking to be sure that the bread is getting toasted without burning. If the bread looks done but the cheese isn’t melted yet, lower heat to lowest setting, cover, and wait 1-2 minutes. When cheese is melted, put cheesy sides together and set aside. Repeat until all the sandwiches have been made.
Oven (faster!): Heat oven to 350 degrees. Butter one side of each slice of bread. On a sheet pan, lay bread buttered-side down. Cover each slice of bread with a slice of cheese. Bake for 5-10 minutes until bread is toasty and cheese is melted. Put cheesy sides together and set aside.
Step 5
Blend the soup using an immersion blender. Add the cream and taste; add more salt if necessary. Serve immediately!