While it's fun to be the star of your own indie film for a certain period of time, eventually logistics are going to dictate that you'll need to ditch the van and fly to a gig, or a short run of gigs. You may not think this will ever happen to you, but trust me - it will. Even if it only happens once on your personal journey from beat-up Sprinter to tour bus, touring inevitably means that you'll have to experience the wonderful world of air travel with gear. Fortunately for you, I'm here to help you navigate this fun little minefield. I'll break it up into two parts, as there's a lot to cover.
Figuring It Out
Once you've accepted the fact that there's no way you're going to be able to drive from that lucrative college gig in Boston to your SXSW showcase in Austin in the 19 hours you'll have in between them (though while you're up there, you should swing by MIT to see how they're coming along on that transporter technology), your next step should be to figure out what is the absolute minimum you can get away with bringing with you on the flight.
I don't think all this is going to fit in the overhead.
Unless you play upright bass, chances are you'll always want to bring your stringed instruments with you; but you can probably live with some backlined gear, so be sure to find out what the backline situation is at your destination. Can you leave the amps at home? What about the drum kit? A snare, pedal, sticks and cymbals can all be carried on, if that's all your drummer really needs to bring. If you're lucky enough to have a keyboard as part of your rig, can you finagle having one waiting for you on stage? If not, what is the rental situation where you're going? Oftentimes, the cost of renting a piece of gear like an 88-key weighted keyboard for a day is less than the cost of bringing yours with you on the plane -- especially if you don't yet have a flight case for your keys, and would need to get one for travel. TSA-rated flight cases are cheaper than a new keyboard, but they're still expensive.
Make a list of what gear each band member is going to have to bring with them, including luggage. Determine what will need to be checked and what can be carried on, so you'll know how many pieces of luggage each person will need to check.
Now it's time to look at flights. There are two main variables to consider when picking a flight: schedule and price. I'll talk about schedule today, and tackle price in part 2.
This is pretty straightforward. What time do you need to be at your destination? Work backwards from there, allowing an hour to get off the plane, get your gear from bag claim, and either pick up and load your rental vehicle, or meet up with whomever is driving you and load up their car. How far from the airport is the gig? Add in a cushion for traffic. Then add a minimum of an hour for flight delays.
Pretty early on in my tour management experience, my mantra became "it's always better to be early than late". Getting to the gig 5 minutes after doors were supposed to open will take years off your life (not to mention your career), whereas having a couple hours to kill in a local coffee shop or napping on the green room couch is a much less stressful way to go.
Once you've worked out your ideal arrival time, see which flights fit that schedule. The cardinal rule of traveling on the day of the gig is to always fly non-stop wherever possible. This will help you avoid the fun of getting to your destination after a tight connection and discovering that while your sprinting sweaty selves made it to the plane in Chicago, your gear did not.1 If you can't get a non-stop flight, consider flying the previous day if you can. Even arriving in the wee hours on the last flight in is sometimes better than cutting it close on the day of a big gig.
In part 2, I'll talk about the all-important Price factor. Until then, if you have any tips of your own, please leave them in the Comments!
1 Funny (not) story: One summer we were traveling from Houston to Albany for back-to-back outdoor festival gigs, and the only way to get there was via Chicago. We had plenty of time between flights in Chicago, but when we arrived in Albany nothing at all appeared on the baggage belt - not just our gear, but nothing, period. Turns out there was a "worker action" happening amongst the baggage handlers in Chicago, and they'd decided not to load anything onto our plane before takeoff. And it was 60 minutes before sound check, and the festival did not provide backline.
Fortunately our trumpet player never lets his horn leave actual contact with his body, so he had that. And by total luck, our drummer was from the area and was able to call a buddy to deliver a kit to the stage. So all we needed was a keyboard. Guitar Center to the rescue!! I won't go into the details, but let's just say that we created a new retail concept called the "GC 14-day rental", and I'm now black-flagged in their system. But it was worth it for the show to be able to go on.