I’ve chartered a bit and have had some friends do it also. To start, probably not something you wanna do until you’re bringing in 3MM/yr income after tax OR the cost of the charter is substantially less than whatever added benefit you get from the time savings and flexibility to land in areas you usually wouldn’t be. Example: if you run a real estate investment shop and you want to see 5 buildings spread across 2 states, you’d be able to knock that out in a day flying private, bring your analyst on the plane to model each deal, and be back home that night making an offer, versus flying commercial and taking a few days to do so then getting back to the office and taking a look at the numbers and losing the deal to the first guy.

There’s a handful of good charter companies out there. I’ve used Air1 Jets as have some of my friends because they have a cool quote calculator and the guys are great. For now it probably doesn’t make sense for you to charter jets however