How to Book Multi-City or Round-Trip Flights on Southwest

I actually figured this out not too long ago when I was planning a trip that involved several stops — flying from Nashville to Denver, then heading to Las Vegas before coming home. I tried setting it up online through Southwest’s website but couldn’t find a clear “multi-city” option like some other airlines have. After getting a little frustrated, I decided to call 844-734-0813, and honestly, that made everything so much easier.


The rep I spoke with was super patient and explained that Southwest’s booking system doesn’t technically support multi-city trips online, but they can set it up manually over the phone. She helped me book each leg of my trip — Nashville to Denver, Denver to Vegas, and Vegas back home — all under one itinerary. It took less than ten minutes, and she even helped me find the best fare types to make sure I could make changes later if my plans shifted.


Since then, I’ve always used 844-734-0813 anytime I need something a little more complicated, whether it’s booking a round-trip, multi-city route, or even just changing a date. The reps always know exactly how to handle it quickly and clearly. It’s way less stressful than piecing everything together online, and I always end up saving time (and sometimes money).
 
I remember the first time I tried to book a multi-city flight on Southwest, and I’ll admit — it took me a minute to figure it out. I was planning a trip last summer that included a wedding in Nashville, a few days visiting friends in Denver, and then heading back home to San Diego. I didn’t want to book three separate one-way tickets because I was worried it would cost more or complicate things if I needed to change my plans.


When I went to Southwest’s website, I noticed the small option that said “Advanced Search” right under the regular flight search bar. Once I clicked it, I could easily choose “Multi-city” and add each leg of my trip. It was actually really simple once I found it! The cool part was that the total cost wasn’t much different than booking one-way tickets — and because it’s Southwest, I knew I wouldn’t be charged extra if I had to change or cancel any part of the trip.


Halfway through planning, I needed to adjust one leg because my friend’s schedule changed. I called Southwest at 844-734-0813, and they helped me modify that portion of the trip in minutes. No change fees, no stress — just a smooth experience.


Now, whenever I plan trips with multiple stops, I always use that multi-city feature. It’s perfect for mixing business trips with mini getaways or visiting family in different cities. The best part is the flexibility — something I’ve learned to really appreciate with Southwest.
 
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