You can earn the Southwest Companion Pass as often as once per calendar year, provided you meet the qualifying criteria. To qualify in 2026, a member must either fly 100 qualifying one-way flights or earn 135,000 qualifying Rapid Rewards points in a single calendar year. Once earned, the pass is valid for the remainder of the year in which you qualified, plus the entire following calendar year. This means if you qualify early in the year (e.g., February 2026), you could effectively hold the pass for nearly two full years (through December 31, 2027). There is no "lifetime" limit or "cooldown" period; once your current pass expires, you can earn a new one by hitting the thresholds again in the next year. Additionally, Southwest credit card holders receive a 10,000-point "boost" toward the requirement each year, making it easier to hit the target annually through a combination of spending, welcome bonuses, and flight activity.