In a large pot over medium heat, heat oil. Season the ground meat with salt and pepper and cook until browned, about 5 to 10 minutes. Stir to prevent ticking and burning.
Add carrots, onions, and garlic. Cook, stirring occasionally, until carrots soften, about 5 minutes. Stir in chilli powder until well combined.
Pour in the tomatoes, cherries, diced chipotle, bay leaves, and water. Mix together until the ingredients are venly distributed and bring to a boil. Once boiling, reduce heat and allow chilli to simmer, stirring just once or twice until the chili thickens. This will take about 10 to 15 minutes. Finally, add the beans and mix together, cooking for an additional 2 minutes.
Remove the bay leaves and discard. Add in the reserved chipotle sauce and give a final mix. Divide the chili among bowls and top each with some yogurt and cilantro. Serve warm, with cornbread or other desired accompaniment.