Supervisor Ramp - MDW - Chicago, IL
Posted on October 24, 2025
Southwest Airlines, a renowned leader in the airline industry, is committed to providing employees with a stable work environment fostered by equal opportunities for learning and personal growth. As a company, Southwest Airlines encourages creativity and innovation to continually enhance its operational effectiveness and maintain its competitive edge in the market. The culture at Southwest Airlines is deeply rooted in values of respect, concern, and care, not only for its customers but equally for its employees. This supportive atmosphere ensures that team members feel valued and empowered to contribute meaningfully to the organization.
Southwest Airlines operates as a major U.S. airline, known for its friendly customer service, reliable operations, and affordable air travel. It connects people across the United States and beyond, focusing on providing a seamless travel experience. The company’s promise to its employees includes opportunities for advancement, competitive pay, and comprehensive benefits that support overall well-being and financial security.
The Ramp Supervisor role within the Ground Operations department is pivotal to maintaining Southwest Airlines' high standards for on-time arrivals and departures. In this leadership position, the Ramp Supervisor manages a team of Ramp Agents and ensures that all ramp operations are conducted safely, efficiently, and in compliance with regulatory standards. The supervisor plays an essential role in fostering a culture of safety and teamwork, guiding agents through coaching and development while prioritizing operational excellence and customer satisfaction.
This position offers a competitive hourly pay rate ranging from $34.94 to $36.39, dependent on qualifications and experience, along with the potential for overtime and shift premiums. Additionally, Southwest Airlines provides eligible leadership and individual contributor roles with discretionary bonus opportunities, enhancing earning potential. Benefits include health insurance coverage from day one of employment, retirement savings plans with company match, potential profit-sharing, and privileges such as free flights on Southwest’s network.
Ramp Supervisors work assigned shifts based on seniority, which may include early mornings, late evenings, weekends, and holidays, reflecting the dynamic nature of airline operations. U.S. citizenship or valid authorization to work in the U.S. is required, along with the ability to obtain necessary security badges and comply with Department of Transportation drug and alcohol policies.
The ideal candidate for this role will possess comprehensive knowledge of airline operations and management principles, coupled with strong leadership and communication skills. Responsibilities encompass coordinating ground support activities, overseeing equipment maintenance, ensuring safety compliance, monitoring staffing and scheduling, and managing performance metrics. The Ramp Supervisor also handles administrative duties including payroll oversight, labor contract administration, and safety program implementation.
Southwest Airlines values diversity and inclusivity, committing to fair hiring practices without regard to legally protected characteristics. Leaders at Southwest are expected to model the company’s cultural values, support employee growth, and contribute to a positive and safe working environment. This role is crucial in upholding Southwest Airlines’ reputation for excellence and customer-centric service at one of the nation’s busiest airports.
                - Must be a resident of Illinois or Indiana
 - Must not have been interviewed for the Supervisor Ramp position at MDW in the last 12 months and not selected
 - U.S. citizenship or current authorization to work in the U.S.
 - Must be able to obtain a SIDA badge and meet airport security requirements
 - Valid U.S. driver's license
 - Must comply with the Department of Transportation drug and alcohol testing program
 - Availability to work shifts including early mornings, late evenings, weekends, and holidays
 - Ability to lift and move items weighing 70 pounds regularly and 40-50 pounds repetitively
 - Ability to work outdoors in inclement weather
 - Ability to communicate effectively in English
 - Ability to use computers and office productivity tools
 - Must maintain a well-groomed appearance
 - Must be at least 18 years old
 - Compliance with company attendance standards
 - No current or future work authorization sponsorship available
 - Able to obtain GSC qualification and possibly Customs Seal if required.