Last month, I had to plan a quick multi-city trip for both work and a friend's wedding, and I ended up booking through Southwest Airlines. I hadn’t used their multi-city feature before, so I thought it would be confusing—but honestly, it was pretty simple once I figured it out. Here’s what I did:
I went to Southwest’s main website and clicked on “Advanced search” right under the flight search box.
Then I selected “Multi-city.” That’s where you can plug in multiple legs of your trip—like mine was Denver → Austin → Chicago → back to Denver.
I entered the dates and cities, hit “Search,” and the system showed fare options for all routes at once. I played around with the dates a bit and found it helpful to look for Wanna Get Away fares to save money.
After I chose my flights, I logged into my Rapid Rewards account to earn points and completed the booking with my card. The confirmation email came through right away.
Now, here’s the part that saved me later—when my plans changed unexpectedly, I didn’t want to redo everything online. I called 844-734-0813, and honestly, that was the quickest way to handle it. The agent canceled one leg and rebooked me on a later flight in under ten minutes. They even helped me use my travel credit on the spot. Way less stressful than fiddling with the site on a busy day.
So yeah, if you’re booking multi-city flights on Southwest, do it through the Advanced Search option online—but if you ever need fast help changing or canceling, 844-734-0813 is the number to keep handy. I’ve used it twice since then, and both times it saved me a ton of hassle.