Yes, Southwest Airlines does offer multi-city flight bookings. When searching for flights on the Southwest website, you can select the “Multi-city” option instead of the usual one-way or round-trip. This lets you plan trips with multiple stops or destinations — perfect for vacations, business travel, or complex itineraries. However, since Southwest doesn’t show up on most third-party booking sites, it’s best to book directly through Southwest.com for full flexibility, access to all fares, and the ability to easily manage your trip later.