Hawaii doesn't have to be some dream vacation you never actually get after. Airline price wars have made it possible to get there on the cheap. You can often find round-trip flights to Hawaii in the $300s on airlines that aren't going to ding you with a truckload of fees before you land.
Right now, you can find fares flying out of many US and Canadian cities in the $300 range, including flights as low as $345 to Honolulu (HNL), Maui (OGG), Kona (KOA), and Kauai (LIH).
You can find low fares flying out of San Francisco ($345 to HNL, OGG), Seattle ($352 to KOA, $362 to HNL, LIH, OGG), Edmonton ($354 to HNL, $357 to OGG), Vancouver ($355 to HNL, $357 to KOA), Calgary ($356 to OGG, $382 to HNL), Los Angeles ($357 to KOA, LIH), Portland ($362 to HNL, OGG), San Diego ($362 to KOA, LIH, OGG), Denver ($362 to HNL, KOA, LIH), San Jose ($366 to KOA, LIH, $377 to OGG), Winnipeg ($367 to KOA, $374 to HNL), Boise ($460 to KOA, OGG), Nashville ($482 to HNL), Austin ($484 to HNL, $488 to OGG), Kansas City ($496 to OGG), and Indianapolis ($498 to HNL).