How to Book Multi-City or Round-Trip Flights on Southwest
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Planning a trip with more than one stop or looking to lock in a round trip on Southwest Airlines? The booking process might feel a little different than what you’re used to, but the good news is Southwest makes it simple—and flexible—to create an itinerary that works for you.
In this guide, we’ll break down exactly how to book multi-city flights and round-trip flights on Southwest, plus some smart tips to save money.
Here’s the catch: Southwest doesn’t have a “multi-city” search tool like some other airlines. But don’t worry—you can easily create your own multi-city itinerary by booking multiple one-way flights.
This is actually a hidden perk, because Southwest is famous for its no-change-fee policy. If your plans shift, you can change or cancel those one-way flights without penalty (you’ll just pay the fare difference, if any).
Traveler story: A San Diego-based flyer booked a trip to Denver, then Chicago, then Dallas—all with one-way Southwest tickets. The total cost was cheaper than booking a single multi-city itinerary on a legacy airline, and they saved extra with two free checked bags.
Follow these steps to piece together a multi-city trip:
Select “One-Way” under the search options.
Enter your origin, destination, and date. Complete the booking.
Return to the search tool and book additional one-way flights for each leg of your trip.
Once booked, you can link them in the Southwest mobile app to view, check in, and track flights all in one place.
Visual idea: Infographic showing three one-way bookings connecting into one multi-city journey.
If your travel plans are simple—just there and back—round-trip booking is the way to go.
On the Southwest homepage, choose Round Trip as your search type.
Add your departure city, destination, and both travel dates.
Southwest offers three fare types:
Both flights will appear under a single reservation.
Pro tip: Sometimes two one-way tickets cost less than a round trip. Always compare before booking.
Traveler hack: One flyer rebooked after a fare sale and scored $120 in travel credits for future trips—no fees, no hassle.
Southwest doesn’t have a dedicated multi-city tool, but their one-way model makes it easy to build your own custom itinerary. For simple travel, their round-trip option is straightforward and flexible.
Bottom line: Whether you’re planning a weekend getaway or a multi-stop adventure, Southwest makes it easy—and affordable—to book the flights you need.
Call (831-298-4213) today to get help booking your Southwest multi-city or round-trip flights and take advantage of the airline’s best perks.
In this guide, we’ll break down exactly how to book multi-city flights and round-trip flights on Southwest, plus some smart tips to save money.
Can You Book Multi-City Flights on Southwest?
Here’s the catch: Southwest doesn’t have a “multi-city” search tool like some other airlines. But don’t worry—you can easily create your own multi-city itinerary by booking multiple one-way flights.
This is actually a hidden perk, because Southwest is famous for its no-change-fee policy. If your plans shift, you can change or cancel those one-way flights without penalty (you’ll just pay the fare difference, if any).
Traveler story: A San Diego-based flyer booked a trip to Denver, then Chicago, then Dallas—all with one-way Southwest tickets. The total cost was cheaper than booking a single multi-city itinerary on a legacy airline, and they saved extra with two free checked bags.How to Book Multi-City Flights on Southwest
Follow these steps to piece together a multi-city trip:
Step 1 — Go to Southwest.com or the Mobile App
Select “One-Way” under the search options.
Step 2 — Book Your First Flight
Enter your origin, destination, and date. Complete the booking.
Step 3 — Repeat for Each Leg
Return to the search tool and book additional one-way flights for each leg of your trip.
Step 4 — Manage Them Together
Once booked, you can link them in the Southwest mobile app to view, check in, and track flights all in one place.
Visual idea: Infographic showing three one-way bookings connecting into one multi-city journey.How to Book Round-Trip Flights on Southwest
If your travel plans are simple—just there and back—round-trip booking is the way to go.
Step 1 — Select “Round Trip”
On the Southwest homepage, choose Round Trip as your search type.
Step 2 — Enter Trip Details
Add your departure city, destination, and both travel dates.
Step 3 — Pick Your Fares
Southwest offers three fare types:
- Wanna Get Away: Cheapest, non-refundable, credit if canceled.
- Anytime: Refundable, more flexible.
- Business Select: Priority boarding, bonus points, free drink.
Step 4 — Confirm and Pay
Both flights will appear under a single reservation.
Pro tip: Sometimes two one-way tickets cost less than a round trip. Always compare before booking.Tips to Save on Multi-City and Round-Trip Flights
- Book early: Southwest fares rise closer to departure.
- Watch for sales: Southwest runs frequent nationwide sales.
- Use Rapid Rewards points: Flexible redemption, no blackout dates.
- Check one-way vs. round-trip: Two one-ways can sometimes be cheaper.
- Rebook if fares drop: Southwest lets you rebook at lower prices and keep the credit.
Traveler hack: One flyer rebooked after a fare sale and scored $120 in travel credits for future trips—no fees, no hassle.Why Book Multi-City or Round-Trip Flights on Southwest?
- No change fees = peace of mind if your schedule changes.
- Two free checked bags = big savings on longer trips.
- Flexible credits = canceled flights turn into reusable funds.
- Strong domestic network = easy to connect major U.S. cities.
Final Thoughts — How to Book Multi-City or Round-Trip Flights on Southwest
Southwest doesn’t have a dedicated multi-city tool, but their one-way model makes it easy to build your own custom itinerary. For simple travel, their round-trip option is straightforward and flexible.
Bottom line: Whether you’re planning a weekend getaway or a multi-stop adventure, Southwest makes it easy—and affordable—to book the flights you need.
Call (831-298-4213) today to get help booking your Southwest multi-city or round-trip flights and take advantage of the airline’s best perks.