Brandon's passion for aviation started at a young age. He became involved in the flight simulator and VATSIM communities, which sparked his interest in aviation and eventually led him to earn his private pilot license. Outside of work, he continues to build flight hours, explore new airports, and stay involved in the aviation community.
Southwest Airlines entered Chicago O'Hare International Airport (ORD) on February 14, 2021, with 20 daily departures and returned to Houston George Bush Intercontinental Airport (IAH) the same year after a 16-year absence. Both moves took advantage of pandemic conditions that had emptied gates at airports Southwest could not normally access. Neither lasted. IAH service ended on August 4, 2024, while O'Hare service ended June 4, announced alongside a simultaneous exit from Washington Dulles (IAD).
Southwest already operates the other major airports in both cities. Chicago Midway (MDW) has been a Southwest base for 41 years and will handle up to 244 daily departures serving more than 80 destinations, including all 15 markets the carrier flew from O'Hare. Hobby Airport (HOU) is a Southwest base where the airline is the dominant operator. At O'Hare, Southwest held roughly 1.9% of the market against two carriers running connecting hubs. The airline's own statement described operating there as "challenging."
Two Entries, Two Exits In Five Years
Southwest Airlines began flying from 
Chicago O'Hare International Airport (ORD) on February 14, 2021, offering 20 daily departures. The timing was deliberate. Pandemic demand had collapsed, legacy carriers had pulled back, and gates at airports that are normally impossible to access had opened up. Southwest moved into O'Hare and returned to Houston George Bush Intercontinental Airport (IAH) the same year, ending a 16-year absence from the airport it had last served in 2005.
Houston went first. On April 25, 2024, Southwest announced it would close four stations effective August 4, naming Bellingham International Airport (BLI), Cozumel International Airport (CZM), Syracuse Hancock International Airport (SYR), and IAH. As reported by The Houston Chronicle, CEO Bob Jordan framed the decision in the carrier's first-quarter earnings release, saying Southwest had "intensified our network optimization efforts to address underperforming markets" and had "made the difficult decision to close our operations" at the four airports. The second attempt at IAH lasted roughly three years.
Chicago followed two years later. Southwest published an end-of-service notice on March 13, 2026, announcing that all flights to, from, and through O'Hare would cease on June 4. The same notice covered Washington Dulles International Airport (IAD), where Southwest had operated since October 2006. Passengers received rebooking and refund options by email. A spokesperson described both exits as part of the airline's ongoing effort to refine its network, and the carrier's statement was blunt about the reason: "Operating at Chicago O'Hare continues to be challenging, and we are confident we can serve Chicagoland through Chicago Midway." The O'Hare experiment ran five years almost to the week.
Southwest Already Owned The Other Airport In Both Cities
Southwest has flown from Chicago Midway International Airport (MDW) for 41 years. It is one of the carrier's largest and most established bases, and the airline will operate up to 244 daily departures from it, serving more than 80 destinations. Every one of the 15 markets Southwest served from O'Hare is already served from Midway. When Southwest announced the O'Hare exit, it directed affected passengers to Midway, Milwaukee Mitchell International Airport (MKE), and Indianapolis International Airport (IND), all airports where it already operates.
The Houston situation was structurally identical. William P. Hobby Airport (HOU) is a Southwest base where the carrier is the dominant operator, and it had been for decades before the IAH return. Southwest built Hobby into a Houston stronghold using the same formula it used at Midway: take the close-in secondary airport that network carriers had largely vacated, flood it with frequency, and compete on fares and convenience rather than connecting breadth. The model worked at both airports for years.
Adding the larger airport in each city created a problem that does not exist when Southwest enters a new market. A passenger in Chicago choosing between Southwest at O'Hare and Southwest at Midway is not a passenger Southwest gained. The airline was splitting its own Chicago demand across two facilities while paying for gates, staff, and ground equipment at both.
At O'Hare, it was doing so with an operation small enough that it could not compete on schedule breadth against United or American, and at Midway it already had the frequency and destination count that made Southwest worth choosing in the first place. The incremental traffic O'Hare generated had to exceed what it cannibalized from Midway to justify the cost, and across five years it did not.
Subscale Against A Fortress Hub
Southwest was a minor operator at both airports. O'Hare is a connecting hub for both United and American, which together control the majority of gates and run schedules organized around banks of arrivals and departures timed to feed one another. Southwest served 15 destinations from the airport. A passenger connecting from a smaller Midwest city through O'Hare to an international destination was flying United or American end to end, because Southwest does not operate a connecting bank structure there and has no long-haul international network to feed.
That left local origin and destination traffic, which is the only market a point-to-point carrier can address at an airport it does not hub. Chicago generates large volumes of it, but Southwest was pursuing that traffic with a schedule far smaller than either network carrier's at the same airport. The DWU Consulting case study on the exit described Southwest's position as constrained largely to origin-and-destination passengers, which is the structural limit on what the operation could have grown into.
Houston produced the same outcome. IAH is United's hub, giving it a connecting operation Southwest could not replicate at the airport. Southwest's IAH station was small enough that the carrier closed it as part of a group of four underperforming stations, listed alongside Bellingham, Cozumel, and Syracuse rather than treated as a strategic market in its own right. Southwest has built successful positions at airports across the country, but it has generally done so by becoming the dominant or near-dominant carrier at each one. At O'Hare and IAH it was neither.
The Operating Environment Works Against The Model
Southwest did not publish a detailed explanation for why either airport did not work operationally. What it did say was consistent and direct. In its statement on the O'Hare exit, the airline said that "Operating at Chicago O'Hare continues to be challenging, and we are confident we can serve Chicagoland through Chicago Midway." Fox 32 Chicago reported that Southwest cited the complexities of operating at O'Hare while noting that it continues to serve the region through Midway.
O'Hare is one of the busiest airports in the United States and operates on a scale that is different in kind from Midway, which sits on a constrained site closer to downtown and handles a fraction of the traffic. Southwest's cost structure depends on high aircraft utilization, which means the carrier is more exposed than most to anything that slows an aircraft between arrival and departure. The airline has built its largest operations at airports where it controls enough of the schedule to manage that itself.
A separate development arrived alongside the announcement. The Federal Aviation Administration had called for a potential reduction in flights at O'Hare around the same period, and NBC Chicago reported that it was not clear whether that played any role in Southwest's decision. The Chicago Sun-Times noted that Southwest's statement did not address the FAA's threat to cut flights at the airport that summer. Neither the airline's media statement nor its passenger notice mentioned it, and no source has established a connection between the two.
The Financial Pressure Behind Both Decisions
The two exits came from different financial positions. Southwest reported a net loss of $231 million in the first quarter of 2024, and the IAH closure was announced in that same earnings release. Boeing delivery delays had cut the airline's growth projections, leaving it with fewer aircraft than planned. Bob Jordan's statement tied the closures directly to financial performance, saying the airline had intensified its network optimization efforts to address underperforming markets. Closing four stations at once was a cost-reduction move executed under pressure.
The O'Hare decision came two years later and was framed differently. Southwest described it as part of an ongoing effort to refine its network rather than as a response to any specific result, and the same notice covered Dulles, where the airline had operated since October 2006. By then, Southwest was well into the broader transformation Jordan has called the most ambitious in company history, a program that has also produced assigned seating, extra legroom seating, and checked bag fees.
Both decisions point in the same direction. Southwest entered O'Hare in February 2021 and returned to IAH the same year, during a period when pandemic conditions had freed up access to airports that are normally difficult to enter. As demand recovered and the network carriers rebuilt their schedules, that access became less valuable than it had looked. The airline is now consolidating around the airports where it holds genuine scale, which in Chicago means Midway and in Houston means Hobby.