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.
In this post:
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?
Focus on Food and beer , such as a Burger-King Whopper.
Eliminate all carry-on bags and pre-selected seats .
Maybe NK and B6 and up being pushed to T5 and this gives AA more gate breathing room?
Just want to make you aware. Either there's a glitch in system or Atmos is secretly devaluing partner award. It's on flyer talk since yesterday. Seems to only effecting booking with more than 1 segment. For example: condor BKK to FRA is still 75K in J. FRA to YYZ is still 55K in J. the 2 combined should have been 85K in J. But now it's showing 130K (which is the added up value straight...
Just want to make you aware. Either there's a glitch in system or Atmos is secretly devaluing partner award. It's on flyer talk since yesterday. Seems to only effecting booking with more than 1 segment. For example: condor BKK to FRA is still 75K in J. FRA to YYZ is still 55K in J. the 2 combined should have been 85K in J. But now it's showing 130K (which is the added up value straight up and "first class price starting from" on Alaska award chart). So either system glitch moving everything to the wrong bracket/ wrong addition. Or Alaska is doing no notice deval. Can you get clarification from your contact at Alaska? Thank you. Long time reader and a fan of your writing style.
Isn’t MDW largely maxed out - can’t add more gates or expand the terminal any further? I believe this may have been part of the reason they ventured into ORD. Granted they can upgauge more MDW flights to the larger 738s to add capacity without needing additional gates and I am sure there are some small holes throughout the day where they can squeeze more flights, but I think it’s largely slim pickings when it comes to MDW without ORD in the mix.
IAD is also getting axed.
WN's strategy from 50 years ago of serving airports which other legacy airlines did not serve is still valid. WN simply does not do well in legacy carrier hubs even though many of those hub metros have two or more airports and WN has a "hub" in one of them.
WN acquired AirTran to gain a position in ATL, a single commercial airport metro, and they are now down to...
IAD is also getting axed.
WN's strategy from 50 years ago of serving airports which other legacy airlines did not serve is still valid. WN simply does not do well in legacy carrier hubs even though many of those hub metros have two or more airports and WN has a "hub" in one of them.
WN acquired AirTran to gain a position in ATL, a single commercial airport metro, and they are now down to less than 50 flights from nearly 300 at AirTran's peak.
WN might be able to rebuild its product and network to be competitive w/ legacy carriers but they are only partway through the process and the evidence says they, at best are only trading some lower fare passengers which they no longer want for higher fare business class passengers - but not in highly competitive markets.
and the real story about ORD is that the FAA is now proposing to limit ORD operations to less than what the airport handled in 2025. If that happens - the City of Chicago is fighting it - UA's growth plans at ORD go up in smoke and ORD joins EWR as hubs with little to no ability to grow the number of flights which would be a stunning rebuke of UA's strategies.
Is southwest selling their gates to either AA or UA
not clear yet but they are in terminal 5 so are of little value to AA or UA; WN's gates are adjacent to DL's gates. DL had way more gates than it needed - mostly for overnight airplane parking - so, even if a few of the weaker cats and dogs move from T2 to 5, DL still will likely have more space than it does now.