Skydive Pilot Jobs in Wisconsin
Last updated July 3, 2026
A guide to skydive (jump) pilot jobs in Wisconsin — the drop zones FlyTo1500 tracks as potential employers, what jump-pilot roles typically require, and how to find current openings.
Short answer
Wisconsin has 10 skydiving drop zones in the FlyTo1500 employer database. Jump-pilot hiring varies by drop zone, season, and aircraft, so this page highlights potential employers and how to find current openings. Flying jumpers is a popular, fast way to build turbine and tailwheel time.
Wisconsin snapshot
- Drop zones tracked
- 10
- Major areas
- Madison, Superior, Sturtevant, East Troy, Beloit, Baldwin
- Common role
- Jump pilot (Part 91 / Part 105 operations)
- Typical minimums
- Commercial certificate; many DZs 200–500 hrs
- Common aircraft
- Cessna 182/208 Caravan, Twin Otter, King Air, PAC 750
- Best for
- Building turbine, tailwheel, and PIC time quickly
Counts reflect employers FlyTo1500 tracks. Requirements and hiring vary by employer, aircraft, and season.
Potential drop zones in Wisconsin
Below are employers FlyTo1500 tracks in Wisconsin. Requirements and current openings vary by employer, aircraft, and season — a listing here does not mean an employer is currently hiring.
Seven Hills Skydivers
Madison, WI
Employer FlyTo1500 tracks
Skydive Duluth
Superior, WI
Employer FlyTo1500 tracks
Skydive Freefall Adventure
WI
Employer FlyTo1500 tracks
Skydive Midwest
Sturtevant, WI
Employer FlyTo1500 tracks
Skydive Milwaukee / Sky Knights SPC
East Troy, WI
Employer FlyTo1500 tracks
Skydive The Rock
Beloit, WI
Employer FlyTo1500 tracks
Skydive Twin Cities
Baldwin, WI
Employer FlyTo1500 tracks
Skydive Wisconsin Dells
Reedsburg, WI
Employer FlyTo1500 tracks
Skydive Wissota
Chippewa Falls, WI
Employer FlyTo1500 tracks
Wisconsin Skydiving Center
Jefferson, WI
Employer FlyTo1500 tracks
Want current openings, not just employers?
FlyTo1500 tracks live listings and matches them to your logbook.
Unlock Current JobsWhat these jobs in Wisconsin typically require
- A Commercial Pilot Certificate (single- and/or multi-engine as required)
- A current medical certificate
- Tailwheel or specific type experience for some aircraft
- Comfort with high-cycle, short-flight operations and precise spotting
- Availability on weekends and during the jump season
Jump operations are conducted under 14 CFR Part 105; pilots need at least a Commercial certificate per § 61.129 and a valid medical per § 61.23.
How to improve your chances in Wisconsin
- Get a tailwheel endorsement — many DZ aircraft need it
- Any Caravan or turbine time makes you far more competitive
- Show up in person at the drop zone before the season starts
- Keep your logbook current and be flexible on weekends
- Set up alerts so you catch new jump-pilot openings early
Skydive pilot jobs in other states
All low-time pilot jobs in Wisconsin
Related FlyTo1500 resources
- All low-time pilot job types — CFI, cargo, survey, skydive, banner tow and more
- Flight instructor jobs by location — CFI employers by state and metro
- Best pilot jobs to build flight hours and how to get 1,500 hours
Official sources referenced
FAA rules set baseline certificate and eligibility requirements; individual employers add their own aircraft, insurance, and experience preferences. Always confirm current rules with the FAA and the specific employer.
Frequently asked questions
How do I get a skydive pilot job in Wisconsin?+
Start with the drop zones near you — Wisconsin has 10 in the FlyTo1500 database. Reach out directly before the jump season, and use FlyTo1500 to track current or recent jump-pilot openings that match your certificates and time.
How many hours do I need to fly jumpers in Wisconsin?+
You need at least a Commercial certificate, and many drop zones look for roughly 200–500 hours, sometimes with tailwheel or specific type time. Exact minimums vary by DZ, aircraft, and insurance.
How many drop zones are in Wisconsin?+
FlyTo1500 currently tracks 10 skydiving drop zones in Wisconsin. Whether any is hiring at a given time depends on the DZ, season, and aircraft.
Is flying skydivers a good way to build hours?+
Yes — jump flying racks up PIC and (on turbine aircraft) valuable turbine time quickly, which is why it's a popular hour-building path. See our guide to the best jobs for building flight hours.
Can FlyTo1500 help me find skydive pilot jobs in Wisconsin?+
Yes. FlyTo1500 tracks drop zones and jump-pilot opportunities and lets you compare them against your hours and certificates. FlyTo1500 helps you discover and compare jobs — it does not employ pilots.
Want to know which pilot jobs you actually qualify for?
FlyTo1500 helps you compare low-time pilot jobs based on your hours, certificates, ratings, and job goals — so you can focus on openings that actually match your logbook.
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