Hawaii 
in $370s-$420s RT
AndreiaJFC
Summer? Fall? Or wanna get away right now because the crushing darkness of winter has already taken hold? Â
... Woah, clearly we're also in need of a trip to Hawaii. The best time to head over (outside of summer, of course) is the shoulder season. Timing your holiday in the sweet spot between April-May will give you the best of fewer crowds and dry weather.
Leaves you worrying about not much at all, except for where the best sunset spots are :-)
Jack's take
Denver, you are limited to Dec-Feb trips, but these are some of the cheapest we've seen in a while. Chicago? Looooooads of trip options to choose from makes Jack a happy boy :-)
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