2 separate tickets, learned my lesson!
 

I learned to book everything on one itinerary! OGG-HNL-ORD-DLH

Thought I was being cute for our honeymoon with a Southwest positioning flight OGG- HNL to take advantage of overnight lie flats from HNL- ORD 8 hours.


Ended up having a 5 hour delay so missed our united flight and had to rebook for the next day.
had to book expensive last minute HNL-SFO-ORD-DLH with only the first segment (day flight) being lie flat.
1700 bucks a piece for flight, 370 for another hotel night, 80 for transportation, more food, more vacation time, more daycare yada yada
oh yeah and United lost my luggage somewhere at ORD..
I think I will be in the doghouse for a while.

Ouch ... we recently had an itinerary that originally was going to be miles and cash tickets. I finally said screw it - paid cash for a single itinerary. Things went perfectly of course but the peace of mind was worth it. The one thing I have learned is that if I do do separate tickets I plan for missed ticket to be the cheap ticket.

Sorry to hear that, but it is a lesson that should be put up in flashing lights on the first page of FT!

When did you learn of the five-hour delay on WN? Could you not have booked an OGG-HNL flight on HA to make your flight on UA?

Did you call UA or just change the flights online and pay the fare difference? Most airlines have a "Flat Tire" rule (though I would have done all I could to not divulge that I was delayed because of another airline's flight). They may have been able to assist in rebooking you the next day at least an even exchange rather than making you pay for the additional airfare. Obviously too late to do anything about it this time but at least trying to pass on the info in case there's a "next time".

I could have, the problem was the delay did not start until boarding, and kept getting pushed back half hour at a time. sat on the plane (connected to the gate) for just shy of 4 hours.

the earlier flight was delayed due to mechanical, we were told it would not affect our flight but they had issues "merging" the flights and putting those passengers on our plane and had to enter everyone's details manually into the computer,

That is some good advice, I knew the risks, rewards, and odds so I am not complaining, things happen

I was able to cancel original flight and get a future credit, I called to book the last minute flight (not online) but they did not use the future credit like I asked, so I have to call and try to get that sorted.