Good tip, out of CLE, I know they'll most likely rebook me through BOS which I would try to avoid during holiday just like JFK and ORD if it's MX, if it's WX I can probably deal with it for up to 12 hours.

Although there's no 100% contingency, I have done this before to make it close to 100%. Buy another refundable (or at least reusable) ticket later during the same day with another airline, cancel it once I reach FLL. At the moment the most affordable backup plan is around $300 with Southwest.

If it's not so far I've also done driving to gateway airports (YYZ and ORD) to catch my long haul flights.