Chicago and East Coast to Hawaii ~$250 Each Way

If you’re free to travel after the holidays, from mid-January through mid-February, there are a number of very good deals available today:
Boston

From $563 round trip (all-inclusive).
Alaska Airlines.
No Friday or Sunday travel.
Purchase by December 4.
I used Kayak and Orbitz to find available dates and fares.

Chicago

From $549 round trip (all-inclusive).
Multiple airlines, including Alaska, American, Delta, Continental, United [...]