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I think I will just bring an extra zip lock bag and ask to purchase Ice once I clear security....
Remember TSA will only allow blue ice.
Sterling
I had that cooler when it didn't have what appears to be a hard top. I brought the soft cooler with us on a trip but not the rolling cart.
Nowadays I usually pack one of those Costco insulated bags or I have a Rachael Ray insulated tote bag that folds easily that I use for our beach cooler & an extra carry on for breakables. Like this http://www.amazon.com/gp/aw/d/B0074...lated+tote&dpPl=1&dpID=41P7ILzRI3L&ref=plSrch
Remember that Hawaii is the 50th state, not a foreign country, and you can buy anything there that you can buy on the mainland, so don't be tempted to over-pack.
They also allow frozen bottles of water as long as they are solid. They can't be slushy. I often fly with my lunch bag and one or two small frozen Pepsi bottles. I'm only 30 minutes from the airport, so they stay solid until I get through security. I pull them out of the bag passing through security since they will always ask to see them.
A couple of TSA agents have teased me about knowing that trick. Apparently it isn't well known, but it is specifically described on the TSA website. I've encountered one or two agents that aren't familiar with the allowance, but their supervisor always flags it through if they call someone else over.
I don't know if there is a limit to number. I've never taken more than two.
Sheila
Link from TSA
https://apps.tsa.dhs.gov/mytsa/cib_results.aspx?search=gel%20ice%20pack
Apparently you can take frozen liquids as long as they are completely frozen. Ice cubes would work as long as you pour off any melt water just before going through security. I also like the frozen water bottle idea since zip bags sometimes leak when the ice starts melting, although I have sometimes had problems getting all the melted water out of a bottle if it is near the bottom.