We're in the downslope of Chicago weather eventually leading to another lovely Chicago winter, where the weather will no doubt range from sucky to just plain horrible. And since I'm a fan of not wearing pants, I look forward to discounted airfare to tropical paradises or even just places that are above freezing.
Winter means off-peak airfare and accommodation, and being cheap always helps. Let's look at some example fares for winter:
*St. Thomas from $192 on Spirit ($226 on AA)
*San Juan, PR from $192 on US Airways
*Kingston, Jamaica from $278 on Spirit
*Nassau from $310 on Spirit ($380 on AA/UA)
Fares haven't dropped to Hawaii quite yet - it's my favorite time to go there in December when the weather sucks here. Hawaiians complain that it's "only" in the 70s, but you can mock them for not understanding what cold weather is really like. Not to mention that if you time your winter vacation right, you can miss the Snowpocalypse like I did this year leading to drunken phone calls of "I'm sorry, I can't hear your blizzard over the sounds of my mai-tai being poured."
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