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Only open one new account at a time. Do not open the next account until you have met the minimum charge to receive the bonus. Minimum charge must be met within 90 days of account application: if you open too many accounts all at once, you will not be able to meet the minimum in time and the bonus will be forfeit. Bonus points offers are only available to new card holders (who have not had the same account open in the past 12- or 24-months).
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Some credit card issuers will only open a new account if you have had 5 or fewer new accounts opened in the past 12- or 24-months. Carefully plan the cards that you need to open to achieve your goal, and do not open any new accounts that are not in the plan, including i.e. department store accounts.
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Each adult should sign up for the free HawaiianMiles loyalty program before opening new accounts. Linking the primary card holder's loyalty account numbers to his/her credit account up front will save time later.
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Transfer miles for free between accounts so all miles in same account.
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Verify dates and availabity of each component of your travel plan to avoid booking one component only to find another component is not available during selected travel dates.
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Charge additional hotel nights to Barclaycard Arrival World Mastercard and apply travel credit. Important: must apply travel credit within 120 days of earning, so recommend booking and paying for hotel early with advance booking discount.
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Check out the Big Island plan for airfare alternatives. For example, for two free r/t tickets open two United MileAge Plus VISA and one Chase Sapphire Preferred accounts (no annual fee the first year) instead of Hawaiian Airline accounts and save the cost of the annual fee.