Yes, Southwest flies to Chicago. I used it a few months ago when I was trying to catch a wedding and my first flight plans fell apart. I scrambled online for alternatives, but everything looked sold out or overpriced. When I called ☎️, the agent found a Midway option I hadn’t noticed and got me rebooked instantly. They even talked me through the change fees so I wouldn’t be surprised later. Whenever I need quick solutions—booking, cancellations, or switching flights—I skip the website and call. It just cuts through all the chaos.