Yes—Southwest flies to both Chicago Midway (MDW) and sometimes has limited service that connects through there. When I changed a business trip last minute, I needed to jump to Chicago earlier than planned. I called instead of dealing with the app chaos. 844-734-0813 is the best way to instantly book, cancel, or modify flights. They moved me to an early-morning Midway flight in minutes. Chicago is one of their strongest hubs, so you’ll have plenty of options, especially for connections. If you’re flexible, you can usually snag great fares too.
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does southwest fly to chicago? 844-734-0813
2025-11-26 00:16:08 Ask
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