Yes, I have, several times now.
First time was a trip I could do by boat, and I thought about doing that.
But my boyfriend of that time flew more often, to congresses, and he took me on a short trip beforehand so I could get used to the whole circus in a safe environment.
Since then, I've flown alone than together. Always in Boeing 737's I recall, always decent jets, 2-4 hour flights, to regular EU countries.
I get uncomfortable in situations that are not well directed (e.g. voluntary activities with no plan, no task manager, no goal). But airports are excellent in directing you to the right place asap. From the drop-off to the gate, there are signs, carts, rolling paths, personnel. The goal of the airport is to make flights come and go on time, and people are the variable factor in that, so they provide them with everything to get that nailed. In an airport, I feel determined.
Sitting on the plane and feeling it take off is a next moment where panic could hit. Why does a decent person, born and meant to walk with two feet on the ground, lift off with a crazy big and heavy metal thing to fly at altitudes where it can't even breathe? Why? I could stay on the ground, that's where humans belong! Then I recall that thousands of people have done this before me, in much more dangerous situations than this holiday flight, and I get calm.
The airport on the way out is another thing, but again do not worry. Signs all over the place, albeit in strange languages, or non-existant at all, in crowds of mumbling people... and once you get out, you're in a strange city and you often don't read or speak a word of it. Luckily, pickup friends or taxis are waiting just for that. And I always study the area around the airport, distance to the first city, general payment for a taxi there, main roads the taxi will take to my destination, how the skyline and the buildings should look. If there's a remarkable building close to my residence, in case of getting lost.
So yes, flying at all is a chaotic, stupid, chaotic thing. But I do enjoy how well it turns out every time