AeroCareers Job Posting: Flexible Gig:Charter Flight Attendant(Winter Garden) | Hiring at Southwest Airlines. This is a Full Time role in Winter Garden, FL. Salary: $35 - $45.

Flexible Gig:Charter Flight Attendant(Winter Garden) | Hiring

Posted on March 15, 2026

Winter Garden, FL Full Time $35 - $45

Local Job Overview: Winter Garden

At a Glance

  • Position: Charter Flight Attendant (Flexible/Contract, Winter Garden)
  • Company: Southwest Airlines
  • Location: Winter Garden, FL
  • This Winter Garden-based role is an excellent opportunity for professionals skilled in relevant skills.
  • Our Southwest Airlines team in Winter Garden, FL is growing.
  • Benefit from working in Winter Garden, a key hub for the Aviation industry.

Compensation & Benefits

  • Pay: $35-$45/Hour (approx. $83.2k/Year)
  • Benefits: This role offers competitive pay.
  • Join our Winter Garden team for this flexible role.

Core Focus

  • Core objectives involve your professional skills in Aviation.


The Vibe

Dynamic, highly specialized, and distinctly unique. Step into our charter operations division. If you want to escape the monotony of scheduled airport jobs and traditional airlines jobs, this is the ultimate adventure. You will be flying collegiate and professional sports teams, specialized corporate groups, and executing unique military missions across the hemisphere.

Your Mission

  • Adaptable Logistics: Adjust catering, service flows, and security measures instantly depending on the exact nature of the charter client (e.g., sports nutrition vs. VIPs).
  • Absolute Discretion: Protect the privacy of high-profile teams and guests, operating with extreme tact and strict confidentiality at all times.
  • Safety Command: Execute flawless safety procedures while operating into specialized or off-network airstrips not typically served by commercial flights.

The Payoff

Enjoy highly specialized override pay, a wildly varied roster that keeps every month exciting, and the legendary travel benefits associated with one of the world's most profitable airlines.