Southwest Airlines is pulling out of one of the United States’ busiest airport, and if anything, I’m surprised the airline tried to fly there in the first place.
Southwest pulling out of Chicago O’Hare as of June 2026
As of June 4, 2026, Southwest intends to discontinue flights to Chicago O’Hare Airport (ORD), as the airline will instead focus on Chicago Midway Airport (MDW). The airline states that this decision was made as part of an ongoing effort to refine its network, and that “operating at Chicago O’Hare continues to be challenging, and we are confident we can serve Chicagoland through Chicago Midway.”
I suspect the reference to “challenging” refers to the profitability of routes from the airport, rather than challenges as a result of overcrowding at the airport. With American and United battling it out at O’Hare, the FAA has now ordered flight cuts there.
Southwest currently serves around a dozen destinations out of O’Hare, including flights to several hubs and focus cities, like Austin (AUS), Dallas, (DAL), Denver (DEN), Las Vegas (LAS), and Phoenix (PHX), as well as some other point-to-point routes, like to Fort Myers (RSW).
It’s logical for Southwest to focus on Chicago Midway
The Dallas-based carrier’s history with serving Chicago O’Hare is interesting. Shortly after the start of the pandemic, all airlines looked for new flying opportunities, given how travel demand evolved. Historically, Southwest served Chicago via Midway Airport, but as of 2021, the airline decided to try serving O’Hare Airport as well.
This strategy of serving the major airports where the airline doesn’t have a presence hasn’t really worked out. For example, at the same time Southwest also started service to Houston Intercontinental Airport (IAH), complementing service to Houston Hobby Airport (HOU), but the Intercontinental Airport service was pulled in 2024.
As I see it, Southwest launched flights to Chicago O’Hare (and for that matter, Houston Intercontinental) as a bit of a test, at a transitionary time for the airline. Could Southwest tap into a new customer base by flying out of these major international airports, rather than Southwest’s smaller fortress hubs? Or would Southwest’s existing customer base value the flexibility offered?
Personally the strategy didn’t make much sense to me. Southwest was never going to be able to compete with American or United at O’Hare, in terms of schedule or loyalty. The only way the airline could compete would be on price, and Southwest isn’t in the business of trying to undercut the competition on pricing, as it’s not an ultra low cost carrier.
I also think it’s worth considering that within the past couple of years, we’ve seen Southwest start to allow flights to be booked through online travel agencies. I think that’s also an interesting angle to consider. By flying to the smaller airports, the airline may have sometimes been excluded from search results, based on the patterns with which people research flights.
When you go to Google Flights and search for a flight from “MIA” to “ORD,” you wouldn’t see options to MDW. Has Southwest maybe been trying to see how actually adding flights to the major airports impacts booking patterns? Either way, I would’ve been more surprised if this were a success, and if flying to these airports was the best use of resources (aircraft).
Bottom line
As of June 2026, Southwest Airlines will discontinue flights to Chicago O’Hare Airport, roughly five years after launching service there. Operating a fairly small network out of O’Hare when you have a massive hub at Midway doesn’t seem terribly logical to me, especially when it’s a hub for two airlines. This move follows a similar situation in Houston a while back. The moral of the story is that airlines love their fortress hubs.
What do you make of Southwest cutting O’Hare flights?