December/Xmas Flights from the Prairies

We are planning a trip to Florida for Xmas with my husbands family. We are planning to stagger our trip over 2 weeks (ie, Grandma and Grandpa and I with the grandkids for the whole 2 weeks), one brother in law and fiance for the first week, the other brother in law and wife and my husband for the second week. I found great (and cheap) flights home on Xmas day which are significantly cheaper than the 26th or 27th and we are all fine with coming back that day so that is not an issue. What I am wondering is if I wait to book the flights to Florida will I find any better deals than now? We are looking at going December 10th to 12th and then my husband and his brother and wife sometime the 17th to 19th. I expect we won't find anything better for the 19th and likely the 17th/18th since it is so close to the school break, but wondering about the 10th to 12th. Anyone with experience have any advice? We are flying out of Regina, although one brother in law and wife may look at flying out of Winnipeg as there is a direct flight and they are fine with driving there.

It USED to be that the farther out you booked, the cheaper it was but not so anymore. Like gas pump prices, airline tickets seem to rise and fall pending on fuel costs AND departing/arriving on different days of the week are factors. We fly out of Regina ourselves and, until recently, United has always given us the best deal (despite charging for baggage). United no longer flies directly to Denver out of Regina so our next trip will be with Delta for 11 Jan - 1 Feb 2016. Right now it looks about $450 CDN per person which is way better than Air Canada or WestJet.

There is no Direct Flights from Regina. Westjet via Winnipeg would be your best and cheapest option. Next i would go Delta,but sometimes the delta website wont give u just 1 connection (MSP), so sometimes you will have to call to book. I highly Recommend taking a Westjet or Air Canada Flight due to the long customs line ups currently in american Airports, but if u use a Canadian connection, you can clear US customs in Canada with about only a 15 min wait. And as looking myself for flights around those dates out of YXE (saskatoon) i found the that the 10-14 of december not much cheaper than the 16. Hope this helps

Book ASAP prices will rise closer to 6 months til christmas

Thanks so much for your replies. We are figuring out our dates and I think I will just book and see what happens. Will likely go with Westjet as I know they have a price drop guarantee. It is so frustrating that there are so few options to fly direct out of Saskatchewan to anywhere. If it was the summer I would think about flying out of Winnipeg since it isn't that bad of a drive from Regina and the departing flight to Orlando leaves mid afternoon, so we could just get up early and drive there that morning. However, I'm not willing to risk having to drive in a winter storm for a direct flight and to save a little bit.