I've been through there many times in both directions. Most people refer to the "five summits" of Pitchoff, because that's about how many bumps there are along the way. I think the highest summit is the second one from the East end (I'd check topozone, but my work web connection filters it).
I never really worried about the summit, because I usually am doing the through trip. I believe that the distance to the summit is shorter from the lower (East) trailhead, but the elevation change is probably less from the higher (West) trailhead.
The whole route is extremely worthwhile. All of the "summits", and many spots in between, have excellent views in one or another, or sometimes both directions. The South view is spectacular, of the lakes and Cascade; the north view is equally nice of the Sentinel Range. In addition to the summits, there are also several lookouts to the lakes along the section from the Western trailhead to the Balanced Rocks.
If the trail has not been broken, it could be pretty time consuming. In addition to the up and down, the trail takes several, hard to predict, sudden turns along the ridge. If you don't know it well, you will have to be really careful to watch markers. There is quite a bit of open rock, and a lot of things will look like trail in the current snow conditions. In the summer, it's a quick blast, and fun to run.
If you are considering a loop trip, take a good look at road conditions. The road through Cascade Pass is somewhat dangerous to walk even in the summer, and could be quite dangerous now. If you can get two cars it would be safer.
Have fun! Pitchoff is a lot of people's favorite!
TCD