Tomato Soup: Add the butter to a large pot over medium-low heat until melted.
Add in the onions and cook for 5–6 minutes before adding in the sugar.
Mix and cook for a further 7-9 minutes until browned while occasionally stirring.
Add in the garlic and cook for 1 to 2 minutes, or just until fragrant.
Pour in the tomatoes and stew for 5-6 minutes, add in the chicken stock and then add in the balsamic vinegar.
Transfer the mixture to a blender and blend on high until smooth.
Add the soup back to the pot over low heat and stir in cream, salt, and pepper. Keep it warm.
Grilled Cheese: Add the butter to a large grilled or frying pan over low heat until melted.
Add the brioche and cook for 1 1/2 to 2 minutes or until it is browned and toasted.
Flip the bread over and spread on the fig jam to two slices of bread.
Next, layer on 1 slice of cheddar, 1 slice of gouda, 1 slice of provolone, and 1 slice of prosciutto over the fig jam. Repeat with the other piece of bread with fig jam. Cook for 1 1/2 to 2 minutes or until it is browned and toasted.
Add the bread with nothing on it to the tops of the cheese and prosciutto.
Slice and serve.
Notes
Make-Ahead: The soup can be made up to 2 days ahead for freshness. Grilled cheese is best to serve as soon as it is finished cooking.How to Store: The tomato soup will hold in the refrigerator covered for 5 days. It will also freeze well covered for up to 3 months. The grilled cheese will hold, covered in plastic in the fridge for up to 3 days. It will not freeze well.How to Reheat: Add the soup to a small pot and heat over low heat until hot. For the grilled cheese place on a tray and cover in foil and bake in the oven at 350° for 6-7 minutes or until warm and the cheese has melted.Try serving the tomato soup with croutons for more texture and flavor.Drizzle somecreme fraiche onto the soup to make it creamier.If you want the soup healthier, use no butter or cream in your tomato soup. Add all of the ingredients together and stew it over low heat. Puree it, season it.Try using 100% whole grain bread with a piece of low-fat or vegan cheese for a healthier grilled cheese.If blending the soup in a blender be sure to remove the center cap of the lid from the blender.Remember, soup gets better with time so it will likely be even better the next day.