Preheat oven to 400°F. Line two baking sheets with parchment paper. Toss butternut squash cubes with 1 tablespoon olive oil, salt, and pepper. Spread in single layer and roast for 30 minutes, turning once.
Toss Brussels sprouts with 1 tablespoon olive oil, salt, and pepper on second baking sheet. Roast for 20-30 minutes alongside squash until crispy and golden.
Bring large pot of salted water to boil. Cook tortellini according to package directions. Drain and set aside.
Season chicken strips with smoked paprika, garlic powder, salt, and black pepper. Heat cast-iron skillet over medium heat for 3 minutes, add 1 tablespoon olive oil.
Cook chicken in single layer for 4 minutes without moving, then flip and cook 5 more minutes until cooked through. Remove to plate.
In same skillet, melt butter over low-medium heat. Add minced garlic and cook 1-2 minutes until fragrant. Deglaze with wine or broth if using.
Add cooked tortellini, fresh thyme, and parmesan cheese. Toss to coat thoroughly in garlic butter sauce.
Return chicken to skillet and stir to combine. Add roasted butternut squash and Brussels sprouts. Gently fold everything together. Taste and adjust seasoning.
Serve immediately, garnished with extra fresh thyme and parmesan if desired.