If you love challah bread, you’ll love these Chocolate Chip Cinnamon Challah Rolls! Soft, pillowy, buttery challah dough is stuffed with warm cinnamon sugar and pockets of gooey chocolate, and topped with a light drizzle of glaze.
Challah is my absolute favorite bread because of the buttery, slightly sweet flavor and that light and fluffy texture. When you put these all together, its the perfect combination of flavor and texture. It’s perfect for sandwiches, french toast or just on it’s own with a pat of butter or jam.
Why I love this recipe
This chocolate Chocolate Chip Cinnamon Challah Rolls recipe takes everything we love about challah bread and turns it into a classic breakfast treat, taking your traditional cinnamon roll to the next level. They’re ideal for a cozy weekend breakfast, a special holiday brunch, or even as a decadent dessert to share with friends and family.
What is Challah?
Challah is a traditional Jewish bread, often enjoyed on Shabbat and holidays, known for its rich, slightly sweet flavor and soft, fluffy texture. Made with eggs, flour, sugar, and oil, it’s typically braided before baking, giving it its signature golden, glossy appearance.
What is the difference between regular bread and challah bread?
Challah bread is a richer, bread with a slightly sweet flavor from the added sugar or honey. It also has a softer more tender crumb from the eggs for a fluffier texture than regular bread.
Ingredients in Chocolate Chip Cinnamon Challah Rolls
- 1-1/2 packet active dry yeast
- 1-3/4 cup lukewarm water
- 1/2 cup granulated sugar + 1 tbsp sugar
- ½ cup vegetable oil (can also use avocado oil)
- 5 large eggs
- 1 tablespoon kosher salt
- 8 cups all-purpose flour
- Filling
- 1/2 cup packed brown sugar
- 1 tsp cinnamon
- 3/4 cup semi sweet chocolate chips
- 3 tbsp unsalted butter (softened) + 1 tbsp melted butter
- Glaze (optional)
- 1 cup powdered sugar
- 1 tbsp milk
Instructions for Chocolate Chip Cinnamon Rolls
- In a large bowl, dissolve yeast and 1 tablespoon sugar into 1¾ cups lukewarm water.
- Add the oil and yeast mixture into the bowl of a stand mixer with the dough hook attachment or a large mixing bowl and stir together
- Add 1/2 granulated cup sugar and 4 of the eggs (one at a time) to the mixture until well blended
- Gradually stir in the flour and mix until a smooth dough is formed (about 2-3 minutes). You can also place dough on a floured surface and knead together for 5-6 minutes until smooth.
- Remove the dough from the mixer and place in a large bowl coated with oil. Cover with plastic wrap, and let rise in a warm place for 1 hour, until almost doubled in size. It may need a bit longer rise time, depending on the temperature of the area the dough is placed.
- Pre-heat oven to 350 degrees
- Grease a 9X9 square baking dish or a round cake pan. You can also line with parchment paper
- Punch down the dough and roll out on a lightly floured surface into a 15″wide X 10″ tall rectangle
- Spread the softened butter evenly across the the dough
- Top with brown sugar and cinnamon
- Add the chocolate chips, making sure they are evenly spread over the top
- Starting from the bottom of the dough, tightly roll up into a log shape.
- Using a sharp knife, cut dough log into 2″slices, and place them flat down into the pan keeping them close together.
- Cover and allow to rise for 30 minutes
- Pour 1 tbsp melted butter across across the tops of the rolls and then sprinkle 1 tbsp granulated sugar
- Bake at 350 degrees for 16-18 minutes. Remove from the oven just as they start to turn slightly golden brown. Don’t leave them in too long or they will lose the soft fluffy texture.
- Allow to cool for 15 minutes and add the glaze if using
- Glaze
- In a small bowl, mix the milk with the powdered sugar until a thick glaze forms and pour on top of the baked rolls.
Storage
These are best eaten the same day, however kept at room temperature in an airtight container, they will last 2-3 days. Heat them in the microwave before 30 seconds before serving.
Chocolate Chip Cinnamon Challah Rolls
Ingredients
- 1-1/2 packages active dry yeast
- ½ cup granulated sugar + 1 tbsp
- ½ cup vegetable oil can also use avocado oil
- 5 large eggs
- 1 tablespoon kosher salt
- 8 cups all-purpose flour
Filling
- ½ cup packed brown sugar
- 1 tsp cinnamon
- 1 cup semi sweet chocolate chips
- 3 tbsp unsalted butter softened + 1 tbsp melted
Glaze
- 1 cup powdered sugar
- 1 tbsp milk
Instructions
- In a large bowl, dissolve yeast and 1 tablespoon sugar into 1¾ cups lukewarm water.
- Combine the oil and yeast mixture into the bowl of a stand mixer with the hook attachment or a large mixing bowl using a whisk to mix together.
- Add 1/2 granulated cup sugar and 4 of the eggs (one at a time) to the mixture until well blended
- Gradually stir in the flour and mix until a smooth dough is formed (about 2-3 minutes). You can also place dough on a floured surface and knead together for 5-6 minutes until smooth.
- Remove the dough from the mixer and place in a large bowl coated with oil. Cover with plastic wrap, and let rise in a warm place for 1 hour, until almost doubled in size. It may need a bit longer rise time, depending on the temperature of the area the dough is placed.
- Pre-heat oven to 350 degrees
- Punch down the dough and roll out on a lightly floured surface into a 15"wide X 10" tall rectangle
- Spread 3 tbsp softened butter evenly across the dough
- Sprinkle the the brown sugar and cinnamon on top of the butter
- Add the chocolate chips, making sure they are evenly spread over the top
- Starting from the bottom of the dough, tightly roll up into a log shape.
- Using a sharp knife, cut dough log into 2"slices, and place them flat down into the pan keeping them close together
- Cover and allow to rise for 30 minutes
- Sprinkle 1 tbsp melted butter and 1 tbsp granulated sugar across the tops of the rolls
- Bake at 350 degrees for 16-18 minutes. Remove from the oven just as they start to turn slightly golden brown. Don't leave them in too long or they will lose the soft fluffy texture.
- Allow to cool for 15 minutes and add the glaze if using
- Glaze
- In a small bowl, mix the milk with the powdered sugar until a thick glaze forms and pour on top of the baked rolls.
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