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1) Confused on the checked bag benefit on this card. Does it mean if I use this card to purchase an Alaska ticket, on Alaska's website for Phoenix-Seattle RT, I won't get a free checked bag because I'm not flying to Hawaii?
The Hawaiian Airlines World Elite Mastercard primary cardmember is eligible to receive 2 free checked bags on eligible Hawaiian Airlines and Alaska Airlines operated flights (free checked bag benefit). The primary cardmember must book the Hawaiian Airlines and Alaska Airlines operated flights with their Hawaiian Airlines® World Elite Mastercard® to receive the checked bag benefit. Authorized Users of the primary cardmember do not qualify for the free checked bag benefit. On Hawaiian Airlines, the free checked bag benefit is only available for travel between North America and Hawaii and between Neighbor Islands (interisland). International flights are excluded. On Alaska Airlines, the free checked bag benefit cannot be combined with other free baggage allowances.
2) Approval odds? 750+ score, AAoA 6 years, 2/24, 0 derogs, 100% payments.
It's not worded the best. But my interpretation is that as long as you are flying within or between North America, Hawaii, or the other eligible neighbor islands, you'll get the benefit.