Southwest Airlines Baggage Policy With a generous baggage policy that allows two free checked bags per passenger, each up to 50 pounds and 62 inches (L+W+H) in length, Southwest Airlines delivers excellent value. There is a $75 cost per item for large items (62-80 inches) and overweight luggage (51-100 pounds). As long as they don’t exceed the size and weight restrictions, sporting goods like golf bags and skis are also allowed. One bag and one personal item, like a laptop or pocketbook, are permitted for carry-on luggage. They have more standards and a list of prohibited items on their website. Wheelchairs and strollers, for example, are free of charge when they meet certain criteria.