Gather all ingredients.
Heat oil in a Dutch oven over medium-high. Add bacon and cook until crisp, stirring occasionally, 5 to 6 minutes. Remove bacon with a slotted spoon, reserving drippings in pot.
Add half of beef to drippings in pot. Cook until well browned, 6 to 7 minutes, turning occasionally. Remove browned beef from pot with a slotted spoon, reserving drippings. Repeat process with remaining beef.
Add jalapeños, bell peppers, and onion to drippings in pot; sauté until softened, 5 to 6 minutes, scraping bottom of pot occasionally to release browned bits. Add garlic to pan; sauté until fragrant, 1 to 2 minutes. Stir in tomato paste and cook until darkened, stirring frequently, 2 to 3 minutes. Stir in chili powder, cumin, oregano, paprika, and salt; cook 30 seconds, stirring constantly.
Stir in broth, tomatoes, and beans. Bring to a boil. Return beef and bacon to pot. Reduce heat to maintain a low simmer. Cover and simmer until beef is tender, about 1 ½ hours. Stir cooked bacon into chili.
Ladle chili into bowls. Top with assorted toppings.
