Place poblanos on a foil-lined baking sheet; broil 8 minutes or until charred, turning after 6 minutes. Place poblanos in a zip-top plastic bag; seal. Let stand 15 minutes. Peel and cut chiles into 1-inch pieces.
Sprinkle beef with salt and black pepper; dredge in flour. Heat 1 tablespoon olive oil in a Dutch oven over medium-high heat. Add half of beef to pan; sauté for 5 minutes, turning to brown on all sides. Remove from pan. Repeat procedure with remaining oil and beef.
Reduce heat to medium. Add onion to pan; cook 12 minutes, stirring occasionally. Add garlic; cook 3 minutes, stirring frequently. Return beef to pan. Stir in tomato, oregano, and cumin; bring to a simmer. Cover and cook 1 hour, stirring occasionally. Stir in poblanos; simmer for 45 minutes or until beef is tender, stirring occasionally. Rinse, seed, and chop chipotle. Stir in chipotle and cilantro. Sprinkle with cheese.