Originally Posted by
IAH-OIL-TRASH
8:55am would be fine. Customs/immigration discharges you at the end of the main terminal closest to the inter-island terminal. No more than 10-minute walk to Hawaiian counter. Hawaiian is not *A and does not recognize United status, so yes, you'll have to cough up the $. If you sign up for Hawaiianmiles, inter-island fee is $15 vs $25. Hawaiian uses tag-dispensing kiosks at HNL, but there's plenty of staff there to help. If you have PreCheck, make sure your TT number is entered into you HA record.
I don't know if there's a Hawaiian rep at bag re-check after customs. Maybe someone else has noticed one?
8:55 AM is fine if the inbound flight is on time. HA will have no obligation to transport you to OGG if there is a delay on the inbound UA flight. Having said that, I’ve found their customer service to be quite good, and I expect they’d probably allow you to fly on the next available flight if that were to happen. In the worst possible case, that’s not a terribly expensive flight to buy even at full Y.
When I flew GUM-HNL-OGG, I schlepped my bags to the inter-island terminal personally, even though they were checked through to OGG. If there was an HA rep, I missed him.
OP: It can’t hurt to ask UA if they can tag your bags through to OGG. While the policy is now “*A only,” I’ve seen sporadic reports that this is waived for 1K members. This would likely save you the $15/$25, although you may still need to carry your bags the way that I did.