Chicago gets fewer flights but double the punchlines from Southwest Airlines

Despite recent flight cutbacks in Chicago’s two major airports, Southwest Airlines is rolling out a fresh advertising campaign in the city designed to re-engage local travelers. In an attempt to rekindle its market in one of the nation's largest cities, Southwest is weaving humor into ads that highlight iconic Chicago traits.

According to the Chicago Tribune , the airline's strategy aims to introduce itself anew amid company-wide challenges. This local campaign is part of a broader effort to boost Southwest's post-pandemic business travel presence and repair its image following massive flight cancellations in December 2022.

Reducing flights amidst business revisions

Despite the push to attract travelers, Southwest has reduced flights at Chicago's O'Hare and Midway airports. As reported by the Chicago Tribune , the airline slashed its O'Hare flights by 23%, and Midway saw a nearly 5% reduction in the first nine months of 2023 compared to the previous year. According to DePaul University's Joseph Schwieterman, the director of the Chaddick Institute for Metropolitan Development, these cutbacks reflect efforts to avoid fierce competition from rival hubs.

Southwest is also addressing its business model in response to pressures from investor Elliott Management, demanding changes after a critical financial year. The airline plans to introduce assigned seating by 2026 and will offer new options like extra legroom and red-eye flights while maintaining free checked bags.

As part of its bid to win back customers, Southwest is also seeking to adjust its board structure, although such efforts fall short of Elliott Management's expectations, according to the Chicago Tribune .

Southwest's Chief Operating Officer, Andrew Watterson, explains that these efforts represent long-term investments in key markets like Chicago. "We view Chicago as having a bright future and an integral part of our network," he said.

While Denver is another focus of the ad campaign, the carrier's initiatives underscore the significance of Chicago's market. "It's only a handful of places we’re doing this kind of big push," Watterson added, emphasizing the city’s critical role in Southwest's network strategy.