Whisk together all ingredients for the dressing in a small bowl and set aside.
Preheat oven to 425F. Toss together the cubed squash, olive oil, 3/4 teaspoon salt, and black pepper on the baking sheet and then spread the squash out in a single layer. Roast the squash until tender and golden in places, about 20 to 30 minutes, tossing the squash once halfway through. Cool.
Meanwhile, bring the water to a boil in a medium saucepan, then add the pearl couscous and the remaining 1/4 teaspoon salt. Bring back up to a boil, then reduce heat to simmer; cover the pot and cook until the water is absorbed, about 20 minutes. Remove from heat and cool.
Add the butternut squash, pearl couscous, onion, kale, chickpeas, and salad dressing to a large bowl and gently toss to combine.
How to Store Butternut Squash: Store roasted butternut squash salad in an airtight container in the fridge for up to 4 days.
Vegan Version: To make this vegan, use maple syrup instead of honey in the dressing.
Serving Suggestion: Top this salad with fresh pomegranate arils to make it colorful and festive.