Originally Posted by HNLbasedFlyer

Welcome to FT.

I'd avoid SFO - the COS-DEN-HNL-OGG routing looks the best, although that makes for a very long day. Make sure you have arranged transportation from UA to Hawaiian as they are in completely different ends of the airport.

Another option is 4 people fly COS-DEN-OGG the next day and 1 person fly perhaps the previous day or another routing - there are 4 F seats available the next day.

Or 3 people go COS-DEN-OGG on Jan 30 and 2 go a different routing that are the most mobile

Originally Posted by MSPeconomist

With elderly/ill passengers in the party, I wouldn't try for a tight connection in a big airport.

I assume that driving the COS-DEN leg wouldn't make sense from your location, especially during the time of year you're traveling.

Originally Posted by ExplorerWannabe

I've generally found the DEN-HNL leg to be pretty smooth and relaxing, especially in first.

Probably the most stressful part of the trip will be the connection at DEN. You will generally arrive at the Godawful "temporary" gates and have to hustle to to gate 40 area where DEN-HNL departs. Since you have 2 folks with limited mobility, request carts to pick you up and take you to your gate. You should be able to request that at both DEN and HNL.

I think you're much better off with COS-DEN-HNL-OGG than COS-DEN-SFO-OGG; having 2.5 hours to make your connection in DEN is much better than 49 minutes, especially at that time of year. I've heard them call "final boarding" for DEN-HNL while I was getting off my COS-DEN flight more than once. COS-DEN-OGG would be even better but I think you would be stressed by splitting up your party.