Fly Southwest: MDW to Owensboro, Kentucky

If you're expecting to embark on a journey from the vibrant city of Chicago to the picturesque Owensboro, one of your excellent choices for travel would indeed be Southwest Airlines. Noted for its reputation of being a value-for-money carrier, Southwest offers an assortment of flights, ranging from direct flights to one-way or round-trip options, all designed to enhance your flying experience.

Commencing our comprehensive guide, let’s delve into the domain of airfare. Prices for Southwest flights primarily depend on several factors, including seasonality, booking time, and seat availability. Hence, understanding the dynamics of airfare can help you snag cheap flights and even attractive flight deals, that could save you a significant amount of money. The common wisdom stands - the best time to book your flight is at least two weeks before the journey. This way, the chances of encountering last-minute flight prices, which are usually on the higher side, reduce substantially.

Now, moving on to the flight duration. While direct flights are the quickest way to reach Owensboro from Chicago, there may be times where only connecting flights are available. Layovers can vary from a short period to a few hours, depending upon the flight schedule. As an informed traveler, you would find it beneficial to verify the total time, including any layover, prior to booking to ensure a smooth journey.

A key factor when choosing a flight should be the available seat categories. Southwest offers classes like Business Select, Anytime, and Wanna Get Away. Business Select, similar to a business class, enjoys priority boarding, extra Rapid Rewards points, and a complimentary premium drink. The Anytime fare is fully refundable and changeable with no extra charges, giving fliers increased flexibility. The Wanna Get Away fare is the most pocket-friendly option although it comes with some restrictions.

Any discussion of flights would be incomplete without mentioning baggage allowance. Southwest Airlines hail themselves as the airline “with Bags Fly Free.” This includes your first and second checked bags (weight and size limits apply) and carry-ons. So, whether you're heading out for a business trip or a vacation, rest assured knowing that Southwest's baggage policy is crafted keeping in view the needs of modern travelers.

Additionally, if you're a frequent flyer who prefers Southwest for your traveling needs, their mileage program - Rapid Rewards, is well worth a look. The program permits you to earn points on flights that you can later redeem for Southwest airfare. It is always heartening to get rewarded for your loyalty, isn’t it?

Lastly, it's worth noting Southwest's flight cancellation policy, which boasts of being one of the most flexible in the domestic flights domain. Depending on the circumstances, you can cancel your flight without worrying about a hefty fee. If your plans change, or something unexpected comes up, this policy can be a real lifesaver.

In conclusion, traveling from Chicago to Owensboro via Southwest promises to be a comfortable, economic, and overall pleasant experience. The various options available, right from airfare to flight schedules, and in-flight services to mileage programs, are all aimed at providing a well-rounded journey. Remember, the art of travel lies as much in the journey as in the destination. Happy traveling!