Can You Book Multi-City Flights on Southwest in 2025?

Planning a trip that includes more than one city? You might be wondering if Southwest Airlines lets you book multi-city flights easily in 2025. The good news is, they do, but with a few conditions. 

Whether you’re visiting friends across different states, hopping between business events, or exploring multiple destinations on one vacation, multi-city bookings can help you travel smarter. In this blog, we’ll explain how Southwest’s multi-city flight options work, how to book them online or by phone, when to use points or the Companion Pass, and how to get the best value for your journey, all in one place.

What Exactly Is a Multi-City Flight and Why Choose It?

A multi-city flight is a type of airline booking that lets you fly to multiple cities in one trip, without buying separate tickets for each leg. Instead of booking round-trip or one-way flights, you plan your entire route with several stops, all under a single reservation.

This is a great option for travellers who want to explore more than one destination without backtracking or buying multiple separate tickets. With multi-city bookings, your trip becomes more flexible and well-organised.

Here’s why many travellers prefer this setup:

• One Booking, Multiple Cities: Keep everything in one itinerary instead of tracking different tickets.

• Ideal for Vacation or Work Trips: Great for people attending events in different cities or planning longer holidays.

• Saves Time and Effort: You don’t need to re-enter your details every time you book a new leg.

• May Unlock Better Deals: Some routes are cheaper when booked together compared to separate one-way fares.

If you’re visiting friends, attending business meetings, or exploring nearby cities, multi-city flights can make the entire trip smoother.

Also Read: What is Southwest Airlines' sale 69?

Does Southwest Have a Multi-City Flight Option?

Southwest does offer a multi-city option, but with some conditions. You can find this feature on their official website or mobile app. It’s located under the “Advanced Search” section, where you’ll see the “Multi-City” tab.

Here's what you should know:

• Online, you can usually book up to 2 or 3 segments.

• For more than 3 cities, or complex open-jaw routes (like arriving in one city and leaving from another), you’ll need to call customer service.

• The online tool is great for simple, 2-stop trips, but not for advanced itineraries.

Pro tip: Some frequent flyers say it’s often easier to book separate one-way flights, Southwest doesn’t charge change fees and allows free checked bags.

Is Booking Multi-City Flights with Southwest Cheaper Than One-Ways?

This is a common question, and the answer is: not always. Unlike some airlines that offer special pricing for round-trip or multi-city bookings, Southwest usually prices each leg individually. That means there’s often no big price advantage to booking everything together.

That said, booking your flights as a multi-city itinerary still has benefits: fewer confirmations to manage, a single record for your trip, and easier support in case of changes.

Let’s look at what affects your final price:

• City Pair and Travel Dates: Routes like Chicago to Orlando to Denver may be cheaper than others, depending on the season.

• Fare Type: Southwest has three fare levels: Wanna Get Away (cheapest), Anytime, and Business Select. Prices vary widely.

• Booking Time: Try to book 6–8 weeks in advance for domestic flights and 2–3 months ahead for international ones.

• Day of the Week: Tuesday and Wednesday are usually the cheapest days to fly. Avoid weekends if you want to save.

Also Read: Southwest Airlines Cancellation Policy Explained

What’s the smart move?

Use Southwest’s Low Fare Calendar to explore options for each leg. Then, compare the total price as a multi-city booking vs. booking each leg as a one-way. Sometimes, booking separately can be cheaper, and with Southwest’s free baggage and no change fees, there's no downside.

Can I Use Points or Companion Pass for Multi-City Flights?

Yes, you can absolutely use your Rapid Rewards points and Companion Pass when booking multi-city flights with Southwest. However, the way you apply these perks depends on how you book.

When booking online, you can apply points during the checkout step, but you may need to do it per segment if the full multi-city route isn’t supported under one reservation. This means you’ll have to book each leg separately if the tool limits your itinerary.

When booking by phone, it’s much easier to use your benefits across multiple legs. The Southwest agent can apply your Rapid Rewards points or Companion Pass throughout the entire trip, all in one go.

Here’s what to keep in mind:

• Points can be used per flight leg when booking online

• Phone booking is better for combining benefits across all cities

• Companion Pass works best when everything is under a single reservation

• Your companion still flies for free, except for taxes and fees

Using points or passes can reduce your total cost by hundreds of dollars, especially if your trip covers multiple cities over several days.

Also Read: Book Group Flights on Southwest Airlines

Conclusion: Is Southwest Multi-City Booking Worth It?

Booking a multi-city flight with Southwest is simple for short itineraries, but may need a phone call for more complex routes. If you're only visiting two or three cities, the online booking tool works well. But for anything longer or more flexible, calling Southwest gives you better control, especially when applying points or using your Companion Pass.

The best part? You can mix and match. Some legs online, some over the phone, and all backed by Southwest’s flexible policies. No change fees. Two free checked bags. And the freedom to explore more cities on a single trip.

Ready to plan your trip? Book cheap flights now with Flightsquest and take the stress out of multi-city travel.

FAQ:

1. Can I book more than 3 cities online with Southwest?

Not usually. The Southwest website allows up to 2 or 3 flight legs. For more than that, it’s best to call customer support and have them book your itinerary manually.

2. Is it cheaper to book a multi-city trip or separate one-way flights?

There’s no fixed rule. Sometimes, booking separate one-way flights is cheaper, especially if you're mixing low-fare dates or airports. Always compare both.

3. Can I include international cities in my Southwest multi-city route?

Southwest offers limited international service (mainly to Mexico, Central America, and the Caribbean). For multi-city international routes, call the airline for help combining them.

4. Will I earn Rapid Rewards points on all multi-city segments?

Yes. Whether you book online or by phone, you’ll earn points on each segment, based on the fare type and distance travelled.

5. What if I book overlapping flight legs by mistake?

Southwest may cancel one or both flights automatically if their system detects overlapping bookings. Always double-check flight times to avoid conflicts.