I find it very hard to believe that you'd have any appreciable compression without gale force winds though. And you don't get to "accumulate" minute amounts of cooling either - the temperature of the "chilled" air coming in is the coldest it will get.
For what it's worth (I'm not a physicist), here is my mental model of how I think it works. We are working at equilibrium we don't care about the macroscopic flow of air as it balances out. When the wind blows in the bottle it creates a more ordered arrangement of the air molecules (imagine laminar or vortex) at the neck (zone of low entropy). The internal energy will diffuse toward the region of more order (Second principle). So internal energy of the inside air flows towards the interface where it then diffuse into the nearby flow and get carried away by the wind.
As soon as there is a temperature difference between the inside air and outside air, traditional heat exchanges also occurs at the interface which has an opposite effect.
It’s the same as blowing on your hand with your mouth wide open – the air is hot.
Now, when you blow with your lips pursed the air is cool – Eco-Coolers do the same thing.
Which does feel like it works...
Illustration: http://i.dailymail.co.uk/i/pix/2016/06/10/18/3521DBE60000057...