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!
Challah Grilled Cheese with Onion Confit and Balsamic Glaze ~ Savory Simple ~ www.savorysimple.netChallah Grilled Cheese with Onion Confit and Balsamic Glaze

I have always loved grilled cheese sandwiches. Growing up I remember my mother serving them to me in a classic form; American cheese wedged between slices of white bread, toasted with butter and served with tomato soup from a can. I considered this meal to be the ultimate comfort food (and still do). When Kitchen Play contacted me about creating a brand new sandwich using Land O’Lakes Deli Cheese as part of their 30 Days of Grilled Cheese, I immediately wanted to try something more creative.

I was given the option to use either Land O Lakes® Deli American Cheese or 4 Cheese Italian Blend. The 4 Cheese Italian Blend immediately called out to me with its savory mix of Asiago, Parmesan, Romano and American cheese.  When I visited the deli counter at my local grocery store I sampled this cheese and was immediately blown away by its rich flavor and creamy smooth texture. I knew immediately that I wanted to pair it with onion confit, balsamic glaze and challah bread.

Challah is another comfort food from my childhood and I thought it would be a perfect choice for this grilled cheese.  Thick, soft and slightly sweet with an egg-washed crust, it really doesn’t get any better than Challah. It provides the perfect bed for oozing cheese, bitter sweet caramelized onions and tangy balsamic glaze. If you’ve never worked with balsamic glaze, it can be found at most grocery stores right next to regular balsamic vinegar. It’s a thicker, syrupy version that makes a perfect drizzle on top of cheese. If you are unable to find balsamic glaze you can easily make your own by simmering balsamic vinegar in a saucepan until it reduces to a syrup.

I thought it was also worth mentioning that from April through May 1, Land O’Lakes will donate $1 to Feeding America every time someone pins or repins a Land O’Lakes recipe on Pinterest. That’s eight meals for a hungry family when you pin a recipe—and eight more every time anyone else repins it. Giving goes viral. Find your favorite Grilled Cheese recipe to pin on

Disclosure: This post was sponsored by Land O’Lakes as part of the Kitchen Play Sidecar series. All opinions given are my own.

Print Pin Recipe

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!
Course Main Course
Cuisine American
Cook Time 35 minutes
Total Time 35 minutes
Servings 2 sandwiches
Calories 814
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: 31.6% | Vitamin C: 9.9% | Calcium: 103.5% | Iron: 6.6%

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About Jennifer Farley

Jennifer graduated from the Culinary Arts program at L’Academie de Cuisine, and has worked professionally as a line cook, pastry chef, and cooking instructor. Her cookbook, The Gourmet Kitchen, was published in 2016 by Simon & Schuster.

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