I had this problem too. Here's how I solved it.
When you change the tier in iTunes Connect, it's not enough to then click 'done'. You need to set the schedule to 'Now' and 'None' (for start and end date) and then click the 'Add to schedule' button. Then save.
Cheers,
S
I found this especially confusing as the "Add to Schedule" button is disabled in my browser, even after selecting "Now" and "None". The button only becomes clickable after clicking on the background of the page to deselect the dropdown, which is probably firing some Javascript event that understands to enable the button.
Just to make it painfully clear (because I was still doing it incorrectly, even after reading Stew's answer above), here's a screenshot.
You need to:
This is now much simpler than it was when the question was asked originally. The Features page for your app at App Store Connect has a Plan a Price Change button under your in-app purchase, and when you press that, it’s very clear how to schedule a price change and make it take effect.
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