Skydive Chicago (DEEP DIVE)

Requirements: 1000TT

Sunday Deep-dive! đŸ€ż

A little late for an email, right? đŸ˜…

Well, I almost didn’t send this one to be honest. But we can’t miss a Sunday, can we?

So, I’m breaking precedence here: this one has a 1,000-hour requirement. If you’re not interested, I get it. I’ll see you next week? 😏

But there are still points to be made for us low time guys through today’s interview.

First, you’re not only competing with low timers for some of these jobs: people with (way) more hours will apply too. It’s rare, but it happens and it might be happening more IF the hiring is actually slowing down at the big leagues.

Second, jump pilot is the most fun flying job out there. Doesn’t matter whether you’re flying a C182 or a C208. And today, we have a former Skydive Chicago turbine pilot talk about his experience.

It’s on the higher end of the total time scale, but I also know it’s relevant for some of you who are getting close to 1,000 hours.

Tell us a little about you

I flew skydivers at a turbine DZ from roughly 3/1/23 to 11/1/23. I was coming from flying for a 135 operator in Alaska. My experience at the time was 2,300 total time and 13 hours multi time with a brand new multi engine certificate under my belt. One advantage I had was being a skydiver since 2019 which gave me an insight on how jump ops work and I also knew a lot of the “players” in the industry. The multi engine turbine hours in the twin otters helped greatly in getting me where I am currently as a First Officer on the Embrear Praetor at FlexJet.

Michael, Caravan and Twin Otter jump pilot

What was the job like?

The job was pretty chill, we would start out around 7:30 am on weekends and 10:30 am on weekdays. First we would preflight our aircraft and make sure they were staged for the correct loading areas we were using that day. Then on to confirm “the spot” with the safety and training advisor (where we would drop the jumpers at). After that was all taken care of we would wait for the first load to fill up. Once started for the day it wasn’t unusual to run nonstop until sunset so make sure you packed lunch or you could order lunch over the radio from the onsite restaurant. Restroom breaks were handled during fueling loads. Trained personal would come out and take your seat while you used an outhouse next to where you would fuel.

During weekends and busy weekdays we would have a second twin otter and pilot ready to take up any slack that may occur. It wasn’t uncommon to run both twin otters most of the day. On weekdays that weren’t so busy we would often fly the caravan instead of the otters. Most of our flying was done at home base where I kept a camper and lived for the season. However there were occasional away contracts we would do on weekend that we split evenly among the pilots. Generally they lasted no more than 3 days. Per diem was paid when away from home base and our stay was taken care of.

The experience

What I liked most about being a jumper dumper were the people. I made some of my best friends to this day from working there. If it weren’t for the great staff and friends I feel like the job would have gotten way more monotonous than it needed to be. Probably my favorite days on the job were big ways and records where we would fly formation, normally two skyvans, and two or three otters. Most of these jumps were much higher in altitude and both we and the jumpers would wear oxygen. Management and staff were all fantastic to work with. Safety was always everyone’s top priority.

100% if they’d match my pay and benefits I’d still be flying jumpers. Everyone who is there is there to have a good time cause they love it. Great atmosphere.

Talking numbers

I’ll start off by saying there was talk of a written contract for the season which I never saw nor signed. I had given a verbal agreement to the owner to fly the full season (which of course I upheld). Our schedule was 5 flying days a week. On weekends we would either be primary or secondary pilot. Secondary pilot only flew when primary got over loaded. Our daily minimum was $230 regardless of if we flew or not. After 10 loads we would make $23 on top of our daily minimum per load. On my busiest day I think I flew 28 loads making that a $644 day. Training pay was a flat day rate however I can’t remember what the rate was. When on the road per diem was paid and I believe it was around $40.

Advice for pilots looking to apply

Where I worked there is a hard minimum set by insurance of 1,000 total time. What would set a candidate apart from the rest would be pervious jump pilot experience (think flying jumpers in a 182/206). Turbine engine experience would also be a huge plus but not required. One thing that people often overlook is being involved in the skydiving community. I know it’s not for everyone but if you were thinking about learning to skydive anyway, it’s a great foot in the door to make connections and there is no better way to learn the jumper side of things than to be one yourself. Almost all of the pilots I worked with were also licensed skydivers.

If you find yourself with one of these jump pilot jobs remember this


Flying a jump run is almost identical to flying an upside down LNAV approach. Treat it like one and be precise flying the jump run. We don’t fly in IMC much as jump pilots and it’s important to keep those skill sharp. Also when it’s time to move on the your next job be ready to explain how you basically shot LNAV approaches all day long (20+ a day) in your interview. Be safe, fly safe, and have fun!

What would flying be without the views?

That’s a wrap!

But hey, if you actually WANT to read about “higher” time jobs like this, reply and let me know!

If enough people need this type of content, we’ll try and squeeze some here and there, or just dedicate a day for not-so-low-time jobs. That would include anything requiring over 1,000 hours, like the Part 135 IFR jobs.

We’ll stay focused on sub-1000-hour jobs until then.

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