There are potentially even better deals. JetSuite offers SuiteDeals for as little as $500 each way. You have to sign up on its website, but when I visited, it didn’t have any flights listed. Wheels Up has a program called 8760. You pay $6,900 annually and access empty legs for as little as $320. You also get entry to its hospitality at events at the Super Bowl, The Masters, other high profile confabs, plus an Inspirato Key Membership which normally has a $10,000 initiation fee and then $3,500 annual dues.
The key words here are prop planes, turboplanes, and light jets. Prop planes like the Cessna Caravan are popular because they're roomy (the seats are like business class, and often configured face to face). More popular these days are planes like the six- to eight-seater Pilatus PC-12, and KingAirs, which fly faster and feel more like jets. And then you get into light jets like Learjets, Embraer Phenom 300s, and Citation CJ3s, and Hawkers, all of which are sleeker and more streamlined, and can fly for four to five hours, for slightly longer trips.
Other near-term empty leg deals included Houston to Aspen on a Citation X seating eight for $14,000, not much less than an eight-seat Learjet 45XR for $18,945 with a normal charter. Skyjet, a broker that also offers empty legs had one this weekend from Nassau in the Bahamas to Ft. Lauderdale on a six-seat Phenom 300 for $3,000. Ft. Lauderdale to Key West and Tampa to Ft. Lauderdale, also on a Phenom 300, were being offered at $2,625 each. Chartering a similar aircraft for the same timings the regular way would run around $6,000.
You will be told how much the hold can take on your chosen aircraft and can upgrade if you feel more space is needed. This will generally be far more than that of a commercial airline. You may also need to upgrade if carrying things like golf clubs and skis. If travelling with a gun, you will need to provide a license and the gun and ammunition must be kept separate. It is then at the captain’s discretion whether it can be on board.