Street-Style Grilled Cheddar Cheese Sandwich with Fresh Tomato Soup
This easy-to-make street-style grilled cheese sandwich features melted sharp cheddar cheese toasted to perfection, served with a vibrant homemade tomato soup seasoned with fresh herbs. Ready in under 25 minutes, it’s a comforting American lunch classic elevated with fresh ingredients and simple grilling.
Ingredients
Check ingredients as you go.
- Sandwich
- Soup
Let’s make it
Sandwich
Preheat a skillet over medium heat for the grilled cheese sandwich.
Sandwich
Butter one side of each bread slice evenly. Place one slice, butter-side down, on the skillet.
Sandwich
Layer the sliced cheddar cheese evenly over the bread in the skillet and top with the second slice of bread, butter-side up.
Sandwich
Grill the sandwich for about 3-4 minutes on one side until golden brown and the cheese starts to melt. Flip carefully and grill the other side for another 3-4 minutes until cheese is fully melted and bread is crisp and golden.
Soup
While the sandwich is grilling, heat olive oil in a medium saucepan over medium heat for the tomato soup.
Soup
Add minced garlic and chopped onion to the pan. Sauté for 3-5 minutes until onions are translucent and garlic is fragrant but not browned.
Soup
Add the canned diced tomatoes (with juices) and vegetable broth to the saucepan. Stir to combine and bring to a gentle simmer.
Soup
Add sugar if using, salt, and freshly ground black pepper to taste. Simmer the soup uncovered for 8 minutes, stirring occasionally, to develop flavors.
Soup
Optional: Use an immersion blender or transfer the soup to a blender carefully and puree until smooth for a creamy texture. Return to pot and warm through if needed.
Soup
Ladle the hot tomato soup into bowls and garnish with chopped fresh basil leaves if desired.
Serving
Slice the grilled cheese sandwich diagonally and serve immediately alongside the tomato soup for dipping.
Tips & notes
For extra crispiness, press the sandwich gently with a spatula while grilling. Use a sharp cheddar for better melting and flavor. Fresh basil adds a nice aromatic touch to the soup but can be omitted if unavailable. To save time, prepare soup first and keep warm while grilling the sandwich.
Saving it for later
Store leftover soup in an airtight container in the refrigerator for up to 3 days. Refrigerate leftover sandwich wrapped tightly in foil or plastic wrap for up to 1 day to maintain texture. The soup can be frozen for up to 2 months in a freezer-safe container; thaw overnight in the refrigerator before reheating.
Reheating
Reheat soup gently on the stovetop over medium-low heat, stirring occasionally. Reheat grilled sandwich in a skillet over medium heat or in a toaster oven to restore crispness, flipping once. Avoid microwaving the sandwich to prevent sogginess.
