Most local printing companies can probably do this. It's basically the same as the personalized family calendars you make with photos. My family creates one of the photo type for my inlaws as a Christmas gift each year (with pictures of the grandkids). We've used various different local printers and/or photo developing companies. I've seen them priced higher, but we usually pay right at $20 per calendar, usually only buying one copy.
For a fundraiser with lots of orders, you can probably get a better price. (But still, with each one being customized, it is a fair amount of labor.)
This year, my family just printed ours at home using our color printer and the quality was just as good as the ones we buy. (I have access to spiral binder.) I used a program called "Calendar Creator Plus". The only thing tricky is printing the pages on both sides so that they come out in the right order. (I doubt you'd want to try to mass produce those on a home printer.)
Good luck and keep us posted. Sounds like a fun project.
For images that aren't already digital, you (or your vendor) will need to scan them. But that's easy to do.
Our new principal is from England and her nephew has a really cute custom calendar that their school does. Each child draws a portrait of themselves and they make a calendar from that which includes standard holidays and school dates too. The company they use is based in England (I hope it's okay to post the link - if not I'm sorry) polygonresourcesforschools.co.uk/index.html
We're trying to find a US based company like this. Does anyone know of one or should we just look to local printing companies? Has anyone done this?