Oh, the weather outside is frightful! At least it is here in Chicago right now. Most people feel like they want to plan a wedding during the pleasant weather, but there are advantages to a winter wedding or a holiday wedding. First of all, there is not the competition for dates, so you have a better chance of booking unique, desirable locations for your party. Another advantage is that people come in to spend the holidays with their families, so out of towners have an easier time attending! A further perk is that most event locations decorate for the holidays & that makes for beautiful pictures!
You may also want to consider January or February weddings, even though in the Midwest these can be tricky as far as weather complications. However, the post holiday season can be fun, as it gives everyone something to look forward to, you have a very good chance of negotiating awesome prices & hopefully you can get away to a warm place for your honeymoon!