1) Use the Chase Ultimate Rewards travel portal to book tickets to Hawaii. This is an Expedia-like travel portal, and you can apply your points to the price of the tickets at a rate of $0.015 per point, so 100,000 points is worth $1500. Depending on when you travel, that is probably enough for 2 round trip tickets.

2) Transfer the points to FlyingBlue (Air France and KLM). They are in the same alliance as Delta, so you can book flights to Hawaii on Delta using those points. Round trip tickets are 30,000 points each, so you could book 2 and still have some points left over for hotel redemptions.

https://upgradedpoints.com/redeem-chase-ultimate-rewards-points-for-max-value/#29-Continental-US-to-Hawaii-on-Delta-in-Economy-Flying-Blue

3) Transfer the points to British Airways Avios. They have a partnership with American and Alaska Airlines, and they have a distance based award chart, so if you fly to Hawaii from the west coast it's only 25,000 miles round trip.

https://upgradedpoints.com/redeem-chase-ultimate-rewards-points-for-max-value/#20-West-Coast-US-to-Hawaii-British-Airways-Avios

4) Transfer the points to Singapore Airlines and fly to Hawaii on United. Both are Star Alliance members so you can redeem your Singapore miles with United. 35,000 miles per ticket round trip in economy, or 60,000 miles per ticket round trip in Business Class.

https://upgradedpoints.com/redeem-chase-ultimate-rewards-points-for-max-value/#3-Fly-Between-the-Continental-US-and-Hawaii-KrisFlyer-Miles

5) Transfer the points to Korean Air. They are also a Skypass (like FlyingBlue), so you can redeem on Delta. But they also partner with Hawaiian airlines and Alaska, so you could book tickets on those airlines. 25,000 miles round trip economy.

https://upgradedpoints.com/redeem-chase-ultimate-rewards-points-for-max-value/#36-Fly-to-Hawaii-Mexico-US-Virgin-Islands-and-Puerto-Rico-for-25000-Miles-Korean-Air-SKYPASS


Note, don't transfer the points until you have dates picked and have confirmed availability. Once you transfer them to an airline, you can't transfer them back to Chase, so make sure you can use them when you transfer them.