Tiffany:
I've been at both times and both have pros and cons.
CROWDS: A visit in October usually will see larger crowds than an arrival in January. The exceptions are the holiday weekends of Columbus Day, New Year's, and MLK when crowds are equally busy. Keep in mind, though, that the low crowds in January typically finds Disney scheduling rides for closure due to routine maintenance.
WEATHER: October brings cooler weather but still warm enough for shorts during the day and a light jacket at night. January can bring unpredictable weather within days of each other: you could go without a jacket or need jeans and a coat. If you're flying, this could mean more luggage. Although Disney keeps many of its pools filled with regulated water, you're more likely to enjoy your resort's pool or visit one of the water parks in October.
COST: October is Regular Season compared to most of January which is Value Season. Although ticket prices will be the same, room rates for the trip will be higher in October.
If cost isn't as much a concern, I'd opt for October. The parks and resorts are decorated for fall. Visiting during the week instead of a weekend can reduce the inconveniences of higher crowds and looking at Disney's
special offer of
free dining might help mirror a package in January. With children, wardrobe is easier when there are no extremes in temperature that can affect everyone's mood, but my motto is always, "A bad day at Disney still beats a good day at the office..."
Wishing y'all a magical vacation!
Whitney