In April, Southwest Airlines announced it would cut flights to multiple airports, including Chicago’s O’Hare International. And so far this year, Southwest flights are down at both O’Hare and the carrier’s key hub at Midway.
But Southwest is doubling down on the Chicago market with a new advertising campaign that pokes fun at iconic city staples, like Italian beef, giardiniera and the region’s long winters. The airline is aiming to lure back travelers in Chicago, one of two cities in the country Southwest is targeting as it seeks to reintroduce itself after a turbulent few years.
The new campaign, which will also feature national ads and those highlighting another large competitive market, Denver, and the vacation destination Hawaii, comes as Southwest is locked in a battle with an activist investor seeking control of the company and has begun to revamp its business model, seeking to reverse slumping profits. In Chicago, the carrier is looking to attract new customers to bolster its post-pandemic business travel plans, and to prove to potential passengers the airline has bounced back from widespread, damaging flight cancellations in December 2022.
Elliott Management, Southwest’s second-largest shareholder, has been highly critical of the carrier in recent months and has pushed for leadership changes and an overhaul of the company’s strategy, saying airline executives haven’t adapted to changes in customers’ preferences and failed to modernize the company’s technology, which contributed to Southwest’s December 2022 meltdown. Southwest has responded with some changes to its board, but the changes haven’t gone far enough for the investment fund.
With control of the company at stake, Southwest recently announced a revamp of its quirky boarding and flight policies. Beginning in the first half of 2026, the airline will give passengers assigned seats, ending the hallmark open-boarding system it has used for more than 50 years. Southwest will offer seats with extra legroom for an extra charge, and offer red-eye flights. Bags will still fly free.
Southwest also this year announced it would limit hiring in response to weakening financial results and delays getting new planes from Boeing, pulling out of four smaller markets and cutting service in Atlanta and at O’Hare.
Southwest has long been dominant at the Southwest Side’s Midway Airport, but began also flying out of O’Hare in 2021. The airline, looking to attract more North Side business travel, sought to capitalize on space created as the COVID-19 pandemic led to cuts in flights at the busy airport.
But Southwest has since cut back. This year, the carrier slashed the number of O’Hare flights scheduled between January and the end of September by 23% compared with last year, or by more than 3,400 flights, data from aviation analytics firm Cirium shows.
At Midway, a large hub for Southwest, the airline cut flights by nearly 5%, meaning there were more than 5,700 fewer flights in the first nine months of this year than the same period last year, Cirium data shows.
Some of Southwest’s cutbacks likely reflect the carrier’s desire to avoid intense competition where its rivals have major hubs, like in Atlanta or at O’Hare, said Joseph Schwieterman, director of DePaul University’s Chaddick Institute for Metropolitan Development.
Southwest’s dominance at Midway still leaves it in an enviable position, and travelers are unlikely to notice 5% in cuts there, he said.
“I don’t think there’s any risk that our three-hub status will weaken or change anytime soon,” he said, referring to the large presence of United and American airlines at O’Hare and Southwest at Midway.
Indeed, on a recent Friday afternoon, the sidewalk outside Italian beef shop Mr. Beef in River North was jammed with a film crew hired by Southwest. Inside the shop — the inspiration for the hit TV show “The Bear” — sliced celery sat in a large plastic tub in the kitchen and peppers drained in a colander in the sink, waiting for the next day’s service. But that day the dining room was empty, Mr. Beef closed to film the commercial.
This commercial would show a resident using free checked bags on Southwest to fly Italian beef sandwiches to his dad. Other commercials in the campaign feature a Chicago resident changing her flight to stay in the city to take advantage of balmy 50-degree temperatures in the middle of winter, and a woman packing giardiniera into her checked bag while offering lessons on how to pronounce the name of the condiment.
Another commercial targets the bitterness of Chicago winters, featuring a Chicago resident who shows off a vacation tan while the rest of the city hasn’t seen sunlight in months. The spots also highlight Southwest’s love for “packers” who use free checked bags, much to the chagrin of a die-hard Chicago fan who won’t let the name of the rival football team in his home.
The Chicago cast and crew filmed the spots at locations like North Avenue Beach and in a home’s “frunch room,” said Julia Melle, director of brand and content.
“One thing that has been happening through the pandemic is, our voice had become really rational, and we are a brand that is known for its unique personality and sense of humor and fun and friendliness and hospitality,” Melle said. “And so there’s an opportunity to bring back that lovable swagger to the brand voice.”
The Chicago commercials are intended both to resell prior customers on the company and changes Southwest has made since the 2022 meltdown, and to reach newer generations of travelers, like business travelers who entered the workforce during the pandemic when they weren’t traveling much, Southwest’s Chief Operating Officer Andrew Watterson said.
That includes boosting awareness of Southwest’s presence at O’Hare where, despite the recent cutbacks, Southwest plans eventually to bring back more flights, he said.
Business travelers, a lucrative segment for the industry, were generally slower to return to the skies after the pandemic shutdowns than leisure travelers. Southwest invested in luring more business travelers to the carrier during the pandemic, but overall business travel has changed, Watterson said.
“This kind of business-oriented play for the North Side of Chicago, the business travel didn’t come back,” he said.
Southwest is also targeting Denver in the ad campaign, another large and competitive market for the carrier. Denver is also a fast-growing hub for Chicago-based United Airlines.
Despite Denver’s rapid growth, Chicago remains a big travel market, Watterson said. Southwest continues to see value in having both a North Side presence, at O’Hare, and a South Side presence, at Midway, he said.
“We feel that we are making investments for the long term in Chicago by being in O’Hare and having our market there, and with Midway as well, and growing both in advertising,” Watterson said. “It’s only a handful of places we’re doing this kind of big push, so that’s an indication that at Southwest Airlines, we view Chicago as having a bright future and an integral part of our network.”
The Associated Press contributed.
Leave a Reply