I learned how to book multi-city flights on Southwest the hard way when I was planning a trip to visit family in different states. I wanted to fly from Baltimore to Denver, then head to Phoenix a few days later before returning home — basically a small tour of relatives and sunshine. I assumed I could just choose a “multi-city” option like on other airline websites, but I couldn’t find one on Southwest’s booking page.
At first, I thought I was missing something. After a quick chat with a Southwest rep, I realized the trick — you just have to book each leg separately. So, I booked my Baltimore–Denver flight, then a second one from Denver–Phoenix, and finally Phoenix–Baltimore as a third trip. It sounded like a hassle, but Southwest makes it easy because you don’t pay any change or cancellation fees.
The best part? When my plans shifted last-minute (my cousin’s barbecue got postponed), I was able to change my middle flight without any penalties — just paid the fare difference. Everything stayed under my Rapid Rewards account, and I still earned points for each leg.
Now, when I plan multi-city trips, I just line up my flights manually and use the “Low Fare Calendar” to pick the cheapest dates. It’s a little extra work up front, but the flexibility Southwest gives you makes it totally worth it.
