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Preheat oven to 425°F. Line a large sheet pan with parchment paper for easy cleanup.
In a small saucepan over medium high, combine cranberries, balsamic vinegar, maple syrup, Dijon, orange zest, garlic and salt. Cook for 6–8 minutes, stirring often, until cranberries burst and sauce thickens slightly. Remove from heat.
On the sheet pan, toss Brussels sprouts, delicata squash, and red onion with olive oil, ½ teaspoon salt, ¼ teaspoon pepper, and thyme. Spread into an even layer, leaving space for chicken.
Pat chicken thighs dry and season with remaining salt and pepper. Nestle onto the sheet pan among the veggies.
Brush about half (2.5 Tablespoons) of the cranberry balsamic glaze over the chicken thighs. Roast for 20 minutes.
Remove pan from oven, brush chicken with more glaze, and toss veggies. Return to oven for 15–20 minutes more, until chicken reaches 165°F and veggies are caramelized.
Drizzle any remaining glaze over chicken and veggies before serving.