Couple problems. First, the only segment in your itinerary that United offers complimentary upgrades is HNL -> SFO. Second, Premier Silver is low upgrade priority. Combine that with current travel demand, and your odds on HNL -> SFO are extremely low.
You could look into MileagePlus Upward (miles plus copay). You’d probably end up waitlisted right now, but you might have a chance that way.
Last edited by WineCountryUA; Oct 10, 2022 at 10:35 am
Reason: repaired post