Yep, Southwest flies to Chicago, Illinois—mainly to Midway (MDW). I figured this out when I mixed up the airports while trying to modify a trip last minute. The website was giving me errors, so I called ☎️. The rep quickly sorted out which airport Southwest actually serves, helped me change my ticket, and explained my cancellation options if my plans shifted again. That call saved me from a bad booking mistake. If you're unsure about routes or need fast changes, talking to someone directly is honestly the quickest fix.