When it comes to small planes, weight matters. Don't be surprised when your contact emails you for all passenger weights, and when the pilot organizes seating by weights. (You don't want the three biggest people on the right side, for instance.) Similarly, don't expect to bring two weeks of stuff for a weekend, and definitely mention if you're planning on bringing golf clubs or skis. If they don't fit, check out ShipSticks or LuggageForward, which sends your equipment beforehand for a relatively small fee.
I have worked with quite a few different charter companies over the years and Stratos Jets has been the easiest to work with. I always work with Kerry Hill because she very professional, friendly, and is just down right awesome at her job. I often need last minute trips for my boss and she always gets back to me quickly regardless of what time of day it is. I truely feel she goes above and beyond to make sure every aspect of the trip runs smoothly and everyone is happy. I can't say enough about how much stress is taken out of booking these flights because I know Stratos and Kerry have everything I need covered.
The Early Air Way is known as being one of the best for putting together one-way and empty leg pricing; we actually started in this industry as an empty leg broker. We have widespread access to Omaha transient and overflying aircraft so as to match a one-way or empty leg with your request. For every request we receive for a one-way flight, or a round-trip that would normally require daily minimums, we tap into our One-Way department for special pricing based on availability.
The most economical option is chartering, which doesn't require any cash upfront (other than a deposit) through companies like Tradewind, Sentient, and Solairus, (which we took home from North Carolina). Of course, there are the old standbys like NetJets and Marquis, who sell fractional ownership (like 1/16th) of a single jet for upwards of $100K. One step down from that, pricewise, is the jet card, where you buy a set amount of hours from a company like Nicholas or Private Jet Services, and can use those hours for different planes. Then there are membership models like WheelsUp, where you pay $17,500 as an initiation fee to fly in their fleet, and then a $8,500 annual dues fee starting the second year. It's like a country club—only you're guaranteed access to a KingAir350i or Citation Excel / XLS instead of a golf course.
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.