Finally got it on my third winter attempt. Took my snowshoes but I didn't need them. Left early and had nice hard snow to walk on all the way to the summit.
10/12/2014 Along with Ben Lomond and Willard.
Made the very slight detour on the way back from Ben Lomond and Willard Peak. I can't imagine it added more than 10 minutes to my overall hiking time. From the Skyline trail I ascended the West slopes to the summit and continued on the ridge for a ways until it all but met up with the Skyline trail. Very worthwhile diversion.
Most poeple along this route will just go right by Chilly. The trail to Ben Lomond skirts right along the West side of Chilly and honestly it doesn't really stand out. Just right off the main trail there is a light trail that will take you right along the ridge line. Even though this Peak doesn't stand out it has some awesome views and some unusual and intersting terrain that is worth the extra couple minutes it takes to get to the top. I like most people would have went right past this Peak if not for my time crunch. The one time I am grateful for the lack of time, it is worth checking out.
I've been to Chilly Peak about six times, usually while snowshoeing in late winter or spring.
Did a winter, posthole ascent --- nice and sporty 5 hour hike!