&gt; I don&#x27;t think my price preferences (for flights or really much of anything else) can be boiled down to an algorithm<p>You&#x27;d be surprised how many people are trying, see e.g.: <a href="https:&#x2F;&#x2F;www.kaggle.com&#x2F;c&#x2F;expedia-hotel-recommendations" rel="nofollow">https:&#x2F;&#x2F;www.kaggle.com&#x2F;c&#x2F;expedia-hotel-recommendations</a><p>You could capture one or more ML features for every one of your questions above, plus hundreds more and add the features that define who you are within their customer population. Then the challenge becomes getting the right model and enough data to train it so that 98% of the time it chooses what you would have chosen. Just keep in mind that, if I have enough information to predict which flight you will take, I have enough information to predict who you are voting for, when you are joining a protest, which is the lowest salary you are likely to accept, hell maybe even enough to predict which opportunities to commit a crime you are likely to take... so, here is to hoping that figuring out which flight we want to take remains unreliable.