I would hazard a guess it's going to be a bit difficult with a .jpg file. I don't know much about mapping but can foresee some technical hurdles, such as scaling.
Without knowing if there's a way to make it interactive (probably is with a lot of work), what I would do is probably get it as close to the scale of the same area in Google Maps (with both facing north of course) Then do a screenshot of Google maps and overlay your jpg on top of it using a image program like Photoshop, Gimp or Paint.Net and set the transparency of the top layer low so the other image shows through.
That would be my "quick and dirty" solution just to overlay two maps since it sounds like just a one-time thing you want to do for one specific area. Someone with a little more technical know-how (and patience) than me might be able to provide a better solution, but doing the above couldn't take more than about 15 minutes if you're familiar with an image-editing program. The trickiest part will get the image to be roughly the same scale as Google Maps at one of the zoom levels.