Southwest Airlines has officially left Chicago O'Hare, and from 2026 every one of its Windy City flights runs through Midway instead. For anyone flying Southwest in or out of Chicago, that's now the airport to book.

The move ends a five-year experiment. Southwest first set up shop at O'Hare in 2021, betting it could chip away at United and American during the pandemic slowdown. It never worked out. The two legacy carriers control roughly 80% of flights at O'Hare, and Southwest's share topped out at a modest 1.7%. Between 2021 and 2026 it carried 8.9 million passengers there, but planes flew about 75% full — below the 80% industry benchmark — while FAA summer flight caps and high operating costs squeezed margins further.

Midway tells a very different story. Southwest has been based there since 1985, operates more than 90% of the airport's flights, and its planes average an 82.3% load factor. It moved 17.3 million passengers through Midway between June 2025 and May 2026. Frontier is a distant second with around 3% of flights.

Thirteen routes disappeared with the O'Hare exit: twelve domestic — including Nashville, Austin, Dallas Love Field, Orlando, Tampa, Fort Lauderdale, Fort Myers, Panama City Beach, Baltimore, Denver, Phoenix and Las Vegas — plus one international route to Cancun. The good news for Southwest loyalists is that nearly all of these cities remain core Midway markets: the airport's busiest domestic routes are Atlanta, Phoenix, Orlando, Las Vegas and Denver, with Cancun the top international destination.

For travellers, the practical takeaway is simple. If you liked using O'Hare because it's closer to the north side and has extensive international connections, you'll now need to weigh Midway's convenience against its smaller route map. Midway sits on Chicago's southwest side, roughly a 40–60 minute trip to downtown depending on traffic, and is far easier to navigate than O'Hare. Fares on Southwest at Midway tend to be competitive, and the consolidation should mean a denser schedule on the routes it kept.

If your itinerary requires O'Hare — say you're connecting onto a United or American long-haul — Southwest is no longer an option for that first leg. You'll be booking one of the legacies, Delta, or a low-cost rival like Frontier for that segment.

Story via Simple Flying.