Chicago-Style Bakery Apple Squares Recipe

Irresistible Chicago-Style Bakery Apple Squares Recipe

Decadent Chicago-style bakery apple squares promise a delightful dessert adventure that captures the essence of midwestern comfort.

Imagine biting into a perfectly crafted pastry that blends sweet, tangy fruit with buttery, crumbly textures.

Warm spices dance through layers of tender apples nestled between flaky, golden crusts.

Rich memories of hometown bakeries emerge with each delectable bite you take.

Seasonal ingredients meld into a nostalgic treat that speaks to cherished culinary traditions.

Layers of carefully balanced flavors create a harmonious experience that feels both familiar and exciting.

The magic happens when simple ingredients change into something truly extraordinary.

Explore this irresistible recipe and let your kitchen become a canvas of delicious creativity.

Drinks and Sides to Serve with These Squares

  • Pair with Warm Cinnamon Coffee: A freshly brewed cup of medium-roast coffee with a dash of cinnamon perfectly complements the sweet and buttery apple squares, enhancing the dessert's warm spices.
  • Match with Vanilla Bean Ice Cream: A scoop of creamy vanilla bean ice cream creates a delightful temperature contrast, balancing the warm pastry and adding a luxurious richness to each bite.
  • Serve alongside Caramel Apple Cider: A chilled glass of caramel-infused apple cider echoes the dessert's fruity notes while providing a complementary sweetness that elevates the overall flavor experience.
  • Enjoy with Spiced Chai Latte: A fragrant chai latte with its blend of warming spices like cardamom, ginger, and nutmeg harmonizes beautifully with the apple squares' comforting autumn-like profile.

Apple Square Variations That Add Something Extra

  • Rustic Berry Patch Squares: Swap apple pie filling with a mix of fresh strawberries, blueberries, and raspberries. Add lemon zest to the crust for a bright, tangy flavor profile.
  • Autumn Pumpkin Spice Squares: Replace apple filling with pumpkin puree and mix in cinnamon, nutmeg, and ginger. Sprinkle chopped pecans over the top before baking for extra crunch.
  • Caramel Pecan Squares: Layer caramel sauce between the apple filling and top crust. Sprinkle toasted chopped pecans on top of the glaze for a rich, nutty finish.
  • Maple Walnut Squares: Substitute part of the powdered sugar in the glaze with maple syrup. Add crushed walnuts to the apple filling for a warm, earthy twist.

Bakery Apple Square FAQs

  • Can I use store-bought pie filling for this recipe?

Yes, you can use store-bought apple pie filling, but homemade filling will give a fresher, more authentic taste to your Chicago-Style Apple Squares.

  • How long can I store these apple squares?

These squares can be stored at room temperature in an airtight container for 2-3 days, or refrigerated for up to 5 days. Just make sure to cover them to maintain freshness.

  • Can I freeze the apple squares?

Absolutely! You can freeze the baked squares for up to 3 months. Wrap them tightly in plastic wrap and place in a freezer-safe container. Thaw at room temperature before serving.

  • What if I don't have a cheese grater for the butter?

No worries! You can use a pastry cutter or even two knives to cut the cold butter into the flour mixture. The key is keeping the butter cold to achieve a flaky crust.

Bakery Apple Squares That Taste Like Fall

  • Dive into a nostalgic dessert that brings the warmth of a Chicago bakery right to your kitchen, with layers of buttery crust and sweet apple filling that'll make your taste buds dance.
  • Create a stunning dessert using simple techniques like grating butter and rolling out dough, perfect for bakers of all skill levels who want to impress without stress.
  • Whip up this versatile treat in under an hour, making it ideal for weekend gatherings, potlucks, or surprising loved ones with a homemade dessert that feels like a special occasion.
  • Enjoy the flexible recipe that lets you play with apple filling variations and create a golden, glazed masterpiece that looks and tastes like it came straight from a professional bakery.

What You’ll Need for Chicago-Style Apple Squares

Pastry Dough:
  • All-Purpose Flour: The base for a tender, flaky crust that holds the filling perfectly.
  • Granulated Sugar: Adds a subtle sweetness to the pastry dough.
  • Salt: Enhances the overall flavor of the pastry.
  • Unsalted Butter: Chilled butter creates a flaky, melt-in-your-mouth texture. Choose high-quality, cold butter for best results.
  • Ice Water: Helps bind the dough together without making it tough.
Filling:
  • Apple Pie Filling: Provides the classic fruity center of the dessert. Use pre-made or homemade filling with a mix of sweet and tart apples.
Glaze:
  • Powdered Sugar: Creates a smooth, sweet topping for the squares.
  • Unsalted Butter: Softened butter adds richness to the glaze.
  • Vanilla Extract: Brings a warm, aromatic flavor to the topping.
  • Milk: Helps achieve the right consistency for the glaze.

Baking Instructions for Apple-Filled Pastry Bars

Step 1: Prepare Dough Base

In a spacious mixing bowl, combine:
  • All-purpose flour
  • Granulated sugar
  • Salt

Grate chilled butter using a cheese grater directly over the dry ingredients. Alternatively, dice butter into tiny cubes and blend using a pastry blender until mixture resembles coarse crumbs. Slowly pour ice-cold water, stirring gently until dough forms a cohesive ball without feeling sticky.

Step 2: Chill Dough

Softly knead dough on a lightly floured surface. Divide into two equal portions. Shape each portion into a flat rectangle. Wrap individually in plastic wrap. Refrigerate for minimum 30 minutes to allow dough to rest and firm up.

Step 3: Assemble Apple Filling Layer

Preheat oven to 400°F. Roll out first dough rectangle on floured surface. Carefully transfer to a 9×13-inch baking pan. Spread apple pie filling evenly across the first pastry layer.

Step 4: Create Top Crust

Roll second dough rectangle. Gently place over apple filling. Crimp and seal edges using fingertips. Create several small decorative vents across top crust using a sharp knife.

Step 5: Bake Golden Squares

Slide pan into preheated oven. Bake approximately 40 minutes until crust turns golden brown and edges look crispy.

Step 6: Prepare Sweet Glaze

While squares cool on wire rack, prepare glaze by mixing:
  • Powdered sugar
  • Softened butter
  • Vanilla extract
  • Milk

Drizzle glaze evenly over cooled pastry. Allow glaze to set completely before cutting into delightful squares.

Tips for Tender Apples and Flaky Dough

  • Master Butter Grating: Use frozen butter and a cold cheese grater for the flakiest, most delicate pastry texture that melts in your mouth.
  • Prevent Sticky Dough: Add ice water gradually and stop mixing the moment the dough just comes together to ensure a tender, not tough, crust.
  • Chill for Perfection: Refrigerate dough for at least 30 minutes to relax gluten and prevent shrinkage, creating a more stable and flaky pastry base.
  • Vent Strategically: Cut clean, precise vents in the top crust to allow steam escape, preventing soggy bottoms and ensuring an evenly baked, crisp surface.
  • Glaze with Care: Wait until the apple squares are completely cool before applying the glaze to prevent melting and ensure a smooth, professional finish.

Best Practices for Storing Apple Squares

  • Refrigerate: Store cooled apple squares in an airtight container in the refrigerator for up to 4 days, keeping the glaze intact and preserving the pastry's texture.
  • Freeze: Wrap individual squares tightly in plastic wrap, then place in a freezer-safe container. Freeze for maximum 2 months, ensuring the dessert maintains its delicious flavor and quality.
  • Reheat: Warm individual squares in a preheated 350°F oven for 8-10 minutes, restoring the crust's crispy edges and bringing back the fresh-baked warmth without compromising the delicate glaze.
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Chicago-Style Bakery Apple Squares Recipe

Chicago-Style Bakery Apple Squares Recipe


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4.7 from 27 reviews

  • Total Time: 1 hour
  • Yield: 12 1x

Description

Sweet memories of Midwestern comfort emerge in these Chicago-style bakery apple squares, promising a nostalgic dessert that celebrates classic American baking. Rich pastry layers and caramelized apples deliver a homemade taste that connects generations of home cooks with pure, honest flavor.


Ingredients

Scale

Main Ingredients (Pastry):

  • 4 cups all-purpose flour
  • 1 ¼ cups (2 ½ sticks) unsalted butter, chilled
  • ½ cup (120 milliliters) ice water, plus more as needed
  • 1 tablespoon granulated sugar
  • 1 teaspoon salt

Filling Ingredients:

  • 4 cups apple pie filling (canned or homemade)

Glaze Ingredients:

  • 1 cup powdered sugar
  • 2 tablespoons unsalted butter, softened
  • 1 tablespoon (15 milliliters) whole milk
  • 1 teaspoon vanilla extract

Instructions

  1. Create a robust pastry foundation by blending flour, sugar, and salt in a spacious mixing vessel.
  2. Utilize a cheese grater to delicately shred chilled butter over the dry ingredients, ensuring even distribution through gentle stirring.
  3. Introduce ice water incrementally, mixing until the dough forms a cohesive, non-adhesive texture.
  4. Transfer the dough onto a lightly dusted work surface and tenderly manipulate it into a unified mass.
  5. Partition the dough into two symmetrical portions, then carefully flatten each into rectangular shapes.
  6. Encase the dough rectangles in plastic film and allow them to rest in the refrigerator for a minimum of half an hour.
  7. Extract one dough rectangle and roll it out on a flour-coated surface, then carefully transfer and press into a 9×13-inch baking pan.
  8. Distribute the apple pie filling uniformly across the initial pastry layer, ensuring complete coverage.
  9. Roll out the second dough rectangle and drape it over the apple filling, meticulously sealing the edges by pinching them together.
  10. Create strategic ventilation by cutting several slits across the top pastry layer.
  11. Position the pan in a preheated oven at 400°F and bake until the surface achieves a rich, golden-brown complexion, approximately 40 minutes.
  12. Remove from the oven and transfer to a wire cooling rack, allowing the pastry to reach room temperature.
  13. Craft a luxurious glaze by whisking together powdered sugar, softened butter, vanilla extract, and milk until smooth.
  14. Once the pastry has completely cooled, generously spread the glaze across the surface and permit it to set naturally.

Notes

  • Master the art of grating chilled butter using a cheese grater for a flakier, more delicate pastry texture that melts in your mouth.
  • Refrigerate dough for a minimum of 30 minutes to ensure the butter stays cold, creating layers of buttery goodness in your apple squares.
  • Use a 9×13-inch jelly roll pan for even baking and perfect rectangular cuts that showcase the beautiful apple filling.
  • Create strategic vents on the top crust to allow steam to escape, preventing a soggy bottom and ensuring a crisp, golden-brown finish.
  • Glaze the cooled pastry with a smooth, vanilla-infused powdered sugar mixture for an extra touch of sweetness that complements the tart apples.
  • Allow the glaze to set completely before slicing to achieve clean, picture-perfect squares that are as delightful to look at as they are to eat.
  • Prep Time: 20 minutes
  • Cook Time: 40 minutes
  • Category: Desserts, Snacks
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 12
  • Calories: 300
  • Sugar: 10g
  • Sodium: 150mg
  • Fat: 18g
  • Saturated Fat: 11g
  • Unsaturated Fat: 7g
  • Trans Fat: 0g
  • Carbohydrates: 34g
  • Fiber: 2g
  • Protein: 3g
  • Cholesterol: 40mg
Isabella Rossi

Isabella Rossi

Founder & Culinary Content Creator

Expertise

Recipe Development​, Traditional Irish and European Cuisines, Food Styling and Photography, Culinary Education​

Education

Dublin Institute of Technology (DIT) – School of Culinary Arts and Food Technology

  • Degree: Bachelor of Arts in Culinary Arts
  • Focus: Comprehensive training in classical and modern cooking techniques, kitchen management, and menu development.​

Ballymaloe Cookery School

  • Program: 12-Week Certificate Course
  • Focus: Intensive, hands-on experience emphasizing farm-to-table cooking and sustainable practices.​

Liam is the voice behind many of Craft Meats’ most flavorful features. With roots in Dublin’s smoky barbecue scene and a culinary degree from the Dublin Institute of Technology, he brings time-tested cooking techniques to life. 

His training at Ballymaloe Cookery School sharpened his farm-to-table approach, giving him a deep respect for every ingredient he writes about.

He’s not about overcomplicating the process, just helping you cook meat that’s worth talking about. When he’s not writing or grilling, he’s out foraging or nerding out on regional spice blends to add to his next recipe.

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