This is cumulative (for some, Edit 5 for clarification).
Easy way to get this quickly is in Old Town Level 7.
About mid through the level you will come to a zip-line behind a window.
Jump though the window, zip down and jump through the second window at the bottom. Then just die.
You re-spawn in the room at the top of the zip-line with both windows intact. Rinse and repeat, takes about a minute or two.
Edit 5: This one seems to be hit or miss. Some players report that this achievement, along with the boxes one, might be glitched, so that you cannot unlock this due to normal play but the requirement needs to be met during one level.
Edit: This cannot be missed if you play the game a little longer. It should pop naturally midway through world 2, District Null.
Edit 2: Iggsy81 and Rookie68 report, that the Achievement did not unlock for them. Might be glitched for some.
Edit 3: Gerbasgamer reports, that he/she completed the game without the achievement popping. Using my solution worked, though. Strange.
Edit 4: Everyone commenting on my solution report, that "Cannot be missed" could be inaccurate. Change my mind?