Some programs make it easy to reprice your travel. For example, you can reprice Southwest Airlines flights (although you’ll want to consider the benefits you might lose by doing so, especially since Southwest is charging bag fees as of May 28) by simply changing your booking. This works for Marriott stays as well.
Other programs require you to cancel and then rebook to capture a lower rate. American Airlines’ AAdvantage award pricing tends to change frequently and drastically for itineraries it operates, so I usually recapture a few thousand miles each week when I cancel and rebook upcoming award flights that have dropped in price.
You’ll only want to reprice flights and hotels that are freely (or at least cheaply) cancelable. And unless you’re willing to consider different flights or hotels — which takes more time than simply repricing what you’ve booked — you’ll likely want to just focus on paid rates and dynamic award rates.
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