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Find low fares on Southwest Airlines® flights to destinations in the Midwest.
Learn what all the fuss is about Midwest nice—see which destinations you can fly to in the Midwest region.
Indulge in some lakeside living with a getaway to this resilient, rapidly growing Middle West stalwart that’s chock full of culture, cuisine, and Forest City charm.
See how nice the Midwest can be—explore everywhere Southwest® flies in the region and start planning to check off some of your bucket list trips. Whether you crave the hustle and bustle of a world-class city with a skyscraper-packed skyline or a sleepy town tucked away in the middle of nowhere, there’s something for every kind of traveler to find in the Midwest.
Now serving.
Chicago (O'Hare)
See why the Second City is second to none when you start your adventure in Chicago with service to Chicago O'Hare International Airport or Chicago Midway International Airport.
Your trip comes with low fares and no hidden fees. That's Transfarency®.
We want to make your trip special, so we're taking everything you love about Southwest and bringing it all to your travels. Get everything Transfarency has to offer on your next trip, only with Southwest.
You can use your points to book any seat, on any flight, no exceptions. Any day, any time, any flight, your points are ready to take you to where you want to go.
Your points don’t expire.
You can earn points on flights and on everyday purchases with our partners, which makes getting to your destination easy. No matter when, or where, you earn them, your points won’t expire.
2First and second checked bags. Weight and size limits apply.
3Fare difference may apply.
4Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
5Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
6Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
7Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
8Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
