Since it is January now, it is actually when we consider the best time to sign up two Southwest cards towards Southwest Airlines' potentially lucrative Companion Pass status. In a given year, if you earn 110K Rapid Rewards points, you will be granted Companion Pass status until December 31st of the following year. Companion Pass members can take a guest for free on any Southwest flights - you need to buy your own ticket with cash or points and only need to pay taxes and fees for your companion. You need to designate a companion but can change three times a year. Now if you open one personal and one business Southwest cards and spend $2,000 on it quickly, you will be able to enjoy the Companion Pass benefit for almost two years!
Southwest Visa Plus Personal ($69/year): landing page
Southwest Visa Premier Personal ($99/year): landing page
Southwest Visa Premier Business ($99/year): landing page