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Challah Grilled Cheese with Onion Confit and Balsamic Glaze

This Challah Grilled Cheese with Onion Confit and Balsamic Glaze is a decadent upgrade of a classic comfort food!
Cook Time35 mins
Total Time35 mins
Course: Main Course
Cuisine: American
Keyword: Challah Grilled Cheese
Servings: 2 sandwiches
Calories: 814kcal
Author: Jennifer Farley


  • 2 tablespoons olive oil
  • 2 medium yellow onion, sliced thin
  • pinch of salt
  • 1 cup water, or more as needed
  • 2 tablespoons balsamic glaze, divided (or more to taste)
  • 4 slices challah
  • 1-2 tablespoons unsalted butter
  • 10 slices Land O'Lakes 4 Cheese Italian Blend Deli Cheese


  • Heat olive oil on low in a large skillet. Add the onions with a pinch of salt. Sweat the onions, stirring, until they begin to caramelize. Turn up the heat to medium-low. Once a brown glaze has formed on the bottom of the skillet, pour approximately 2-3 tablespoons of water into the pan to deglaze and use a spatula to scrape up the brown bits and stir them into the onions. Repeat this glazing and deglazing process until the onions have been thoroughly caramelized and taste both sweet and bitter, approximately 25-35 minutes. Use more or less water as needed. Set the caramelized onions aside.
  • Lightly butter all 4 slices of challah and place them on a clean skillet over medium heat to lightly brown on one side. Once browned, it's time to build the sandwich: Flip the bread so that the toasted side is facing up. As the other side begins to toast, layer 2 slices of bread each with 5 slices of Land O'Lakes 4 Cheese Italian Blend Deli Cheese. Divide the caramelized onions on top of the cheese and follow with a generous drizzle of balsamic glaze. Close each sandwich and continue cooking until both sides are golden brown and the cheese is melted.


Calories: 814kcal | Carbohydrates: 19g | Protein: 36g | Fat: 66g | Saturated Fat: 35g | Cholesterol: 164mg | Sodium: 905mg | Potassium: 297mg | Fiber: 1g | Sugar: 8g | Vitamin A: 1580IU | Vitamin C: 8.2mg | Calcium: 1035mg | Iron: 1.2mg