You're standing in the middle of your kitchen, three tabs open on your laptop, trying to figure out how to get from Austin to Nashville, then over to Raleigh, and finally back home without paying for three separate, overpriced one-way tickets. It feels like it should be easy. Most airlines have a big, obvious button for this. But if you’ve spent more than five minutes looking for a Southwest Airlines multi city booking tool on their homepage, you’ve probably realized something annoying.
It isn't there.
Well, it’s not there in the way you expect it to be. While legacy carriers like Delta or United have a dedicated "Multi-City" toggle right next to "Round Trip," Southwest plays by different rules. They always have. This is the airline that still doesn't use assigned seating, after all. To master the art of the multi-stop trip with the "LUV" airline, you have to understand the workaround. It's not a glitch; it's just how their backend system is built.
Let's get into the weeds of how this actually functions.
The Multi-City Myth on Southwest.com
Southwest doesn’t have a multi-city search tool because their entire pricing model is based on "point-to-point" fares. Every flight you book with them is essentially a one-way segment joined together. When you book a round trip, the website is literally just adding the price of Flight A to the price of Flight B. There is no "round-trip discount" like you might find on an international carrier flying to London.
Because of this, Southwest Airlines multi city booking is fundamentally just a series of one-way purchases.
Wait. Don’t close the tab yet.
There is a way to do this that keeps your confirmation numbers organized and makes your life easier, especially if you’re trying to use Rapid Rewards points. You just have to know where the "hidden" portal is. If you go to the Southwest homepage and click on the "Flight" search tool, look for the tiny text that says "Advanced Search" or look for the "Multi-city" option specifically within the booking widget if it's currently being tested in your region. Most of the time, however, the pro move is using the "One Way" booking method repeatedly or using the specific Multi-City link often found in the footer or via the "Help" pages.
Why Bother With Multi-City Anyway?
Maybe you're doing a "triangle trip." You know the one. You have a business meeting in Chicago, but your sister lives in Denver, and you want to stop by for a long weekend before heading back to San Diego.
If you book three separate one-way tickets, you end up with three different confirmation numbers. That’s three emails to track. Three check-ins to remember. Three different times you have to scramble to find your boarding pass in the app while a line of impatient travelers sighs behind you.
When you use a true Southwest Airlines multi city booking flow—which is accessible through their specific multi-city booking page (yes, it exists, it’s just tucked away)—you can often get all those legs under a single reservation. This is huge for organization. It’s also vital if you’re trying to manage your Companion Pass. If you have a companion traveling with you, having everyone on one itinerary makes the "Add Companion" process significantly less of a headache.
The Step-by-Step (The Non-Robotic Version)
- Navigate to the Southwest website. Don't use the app for this; the app is great for checking in, but it’s clunky for complex bookings.
- Look for the "Booking" section. If you don't see "Multi-city" as a radio button next to "One-way" and "Round-trip," click on "Advanced Search."
- This is where the magic happens. You’ll see the ability to add up to three or four segments.
- Enter your first leg. Austin (AUS) to Nashville (BNA) on the 10th.
- Enter your second leg. Nashville (BNA) to Raleigh-Durham (RDU) on the 14th.
- Enter your final leg. Raleigh-Durham (RDU) back to Austin (AUS) on the 18th.
The system will then spit out a list of flights for Leg 1. You pick one. Then it shows Leg 2. You pick that. It feels like a marathon, but it works.
The Pricing Trap
Here is something people get wrong. They think that by grouping these flights, they’ll save money. Honestly? You probably won't. Southwest prices are transparently one-way. The price you see for that Friday night flight to Nashville is the same price whether it’s part of a multi-city itinerary or a standalone purchase. The benefit is purely administrative.
However, there is a catch with taxes. Sometimes, certain segment taxes or 9/11 security fees can fluctuate slightly depending on how the "connection" is timed, but for the most part, you aren't gaming the system here. You're just organizing it.
Rapid Rewards and the Multi-City Headache
If you are a points hound, listen up. This is where things get "kinda" complicated.
Southwest’s system is generally great with points. But when you start trying to mix cash and points on a Southwest Airlines multi city booking, the website might have a literal meltdown. As of right now, you usually have to choose one or the other for the entire itinerary. You can’t really pay for Leg 1 with points and Leg 2 with a credit card within a single multi-city booking flow.
If you find yourself in that situation, just book them as separate one-way flights. It’s not worth the stress.
What Happens When Things Go Wrong?
Let's talk about the "Southwest Meltdown" of 2022. It’s the elephant in the room. When you have a multi-city itinerary and the first flight gets cancelled, the ripple effect is real.
If you booked everything on one confirmation number, Southwest’s system "knows" you are on a journey. If Flight 1 is delayed and you miss Flight 2, a gate agent has more leverage to help you if it's all one "record locator." If you booked them as separate one-ways, the system sees Flight 2 as a completely unrelated event. If you don't show up for it because you're stuck in an airport three states away, you might be marked as a "no-show."
That’s a nightmare.
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Always, always link your flights or book them under one confirmation number if the layovers are short. If you’re spending three days in each city, it matters less. But for tight turnarounds? One confirmation number is your insurance policy.
The Secret "Open Jaw" Alternative
In the travel industry, there’s a term called "Open Jaw." This is when you fly from Point A to Point B, and then return from Point C back to Point A.
Example: You fly from Dallas to New York. You take a train from New York to Philadelphia. Then you fly from Philadelphia back to Dallas.
Southwest is the king of the Open Jaw. Because their pricing is point-to-point, you can book this as two one-way flights and it costs exactly the same as a round trip. You don't even need the multi-city tool for this. Just book a one-way to NYC and a one-way home from Philly. Done.
Things to Keep in Mind Before You Click "Purchase"
- Baggage follows the rules of the day. Even on a multi-city ticket, you have to reclaim your bags if your "stop" is an actual stay. If it's just a long layover (under 4 hours for domestic), they might check them through. But if you’re staying overnight, you’re hauling those suitcases to the hotel.
- EarlyBird Check-In is per flight. If you buy EarlyBird for a multi-city trip, make sure it’s applied to every segment. Sometimes the system only toggles it for the first one. Check the "Review Trip" page carefully.
- The 24-hour rule. Just like any other flight, you have 24 hours to cancel the whole mess for a full refund to your original payment method. After that, it’s Travel Funds (unless you bought Business Select or Anytime fares).
Actionable Next Steps for Your Trip
Stop trying to find a "deal" by bundling cities. It doesn't happen on Southwest. Instead, focus on your calendar.
First, go to the Southwest Low Fare Calendar. Check the individual prices for each leg of your trip. Note down the cheapest days for each segment. Once you have your dates, then go to the Multi-City/Advanced Search tool to piece them together.
If the website gives you an error—which happens more than it should with complex itineraries—don't panic. Just book them as individual one-way flights. You still get your two free checked bags. You still get no change fees. You just have to keep track of a few more emails.
Check your flight status 24 hours before the first leg of your Southwest Airlines multi city booking. If that first flight looks shaky, call the Southwest customer service line (or hit them up on X/Twitter) immediately. It’s much easier to fix a three-city trip before you’ve left your house than it is when you're standing at a kiosk in a crowded terminal.
Keep your confirmation numbers in a notes app on your phone. Screenshots are your best friend. Technology is great until the airport Wi-Fi dies and you can't load your boarding pass.