Preheat the oven to 425 degrees F. Line a baking sheet with aluminum foil.
Roast your Delicata and Brussels Sprouts: Slice your delicata in half longways, and scoop out the seeds. You’ll have two halves that look like boat – perfect for stuffing! Brush the edges of the delicata with 1/2 Tbsp. olive oil, and place it cut side-down on the prepared baking sheet.
Clean brussels sprouts, chop off the bottom, and slice in half. Place halved brussels on the baking sheet with the delicata.
Toss brussels with 1/2 Tbsp. olive oil, then season with salt and pepper to taste. Roast for 20-25 minutes, or until delicata skin is tender and brussels are browned.
Make the Balsamic Kale and Chickpeas: When the oven has 10 more minutes, prepare the kale and chickpeas. Heat 1 Tbsp. olive oil over medium heat. Add kale, salt, and pepper, and sauté until kale softens and is bright green in color. Add chickpeas, oregano, and red pepper flakes, and mix with a silicone spatula or wooden spoon.
Add balsamic vinegar, quickly covering the kale and chickpeas. The balsamic vinegar will instantly get sticky and coat the kale and chickpeas. Once this happens, quickly remove mixture from heat (the balsamic can easily burn).
Assemble your Kale-Stuffed Delicata Squash: Carefully remove baking sheet from the oven. Place squash on a plate. Fill with the Balsamic Kale and Chickpea mixture. Top with roasted brussels sprouts. Drizzle with additional balsamic if desired.