Place bacon in a large skillet and cook over medium-high heat, turning occasionally, until evenly browned, about 10 minutes. Drain bacon slices on paper towels. Chop into small pieces when cool enough to handle.
Bring a large pot of lightly salted water to a boil. Add penne and olive oil and cook, stirring occasionally, until tender yet firm to the bite, about 8 minutes.
While pasta is cooking, melt butter in a large, deep skillet over low heat. Add chopped bacon, garlic, and 1 teaspoon pepper; saute until fragrant, 2 to 3 minutes. Increase heat to medium, add chicken, and cook until chicken is no longer pink in the center and the juices run clear, 5 to 7 minutes.
Add whipping cream, Parmesan-Romano cheese, and remaining 2 teaspoons pepper to the skillet. Stir and cook until heated through, about 3 minutes. Add Colby Jack cheese and stir until melted. Stir in beaten eggs and bring to a simmer. Add drained pasta, stir until coated with sauce, and serve immediately.
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