So my brother is going to yeshivas kayitz (summer learning camp) on the Big Island of Hawaii.
I'll play the jealous older brother.
Paid tickets are over $1,000, so miles it is.
Obviously searching CLE-KOA pulls up nothing at saver levels on AA, AS, CO, DL, UA, and US websites.
The trick is to break it down. Search individual segments.
You need to search gateway cities. Meaning on CO/UA search for DEN, LAX, or SFO to KOA.
On AA search LAX or SFO to KOA.
On AS search SEA to KOA.
On US search PHX to KOA.
On DL search LAX to KOA.
Of course after that you can also search for flights to HNL, LIH, OGG, or ITO (from all the gateways that serve those cities) and then work on getting from those airports to KOA.
Once you find availability from a gateway you just need to piece together a flight from your home city. Be willing to take stopovers!
In the end I was able to piece together CLE-DEN-LAX (stopover for shabbos)-KOA-SFO-CLE for 40K CO miles.
Of course CO.com won't book that. So I booked LAX-KOA-SFO-CLE on CO.com using multiple destinations and then called up CO to add the CLE-DEN-LAX flights to the itin. The agent didn't see CLE-LAX avaialbility until I force fed her the flights and convined her that they really were available for awards. Then they wanted to charge 55K miles because "that's what the computer says." After convincing a manager that this was just a simple itinerary with a stopover (permitted on Hawaii awards) she overrode the computer and allowed it for 40K miles.
It's now bookable online with no phone fee.
Anyway the same strategies apply for flights to anywhere. Search gateways, be willing to take stopovers, search partners and on as many websites as possible, book what you can online and have an agent edit the itin.
Enjoy the free flying!