If you're going to a city you've never been to before, you might not have “a guy” you can call. While roadtrippin’ with a baggie of the green stuff doesn’t usually present much of a problem, smuggling it on a plane means dealing with the increased pressure of uniformed security, x-ray machines, and dogs.
Fortunately, the TSA actually isn’t actually that interested in stealing your stash. They’re just only looking for guns, bombs, and drug mules and will only bust you if they happen find it. So if you’re careful, you can probably get away with it. Heck, people bring it on accidentally all the time.