I usually plug mine into whatever system closest to me has speakers at the time, be it my tv, stereo system, pc, most'o'cheapo portable speakers, guitar amp etc etc
I'm all optical an HDMI, so plug my iPad into my DTS system.....Awesome sound, I've tried a few of the smaller ones, but they just sound tinny, then again, I'm REALLY fussy about sound. When my AV HDMI kit arrives ( didn't come today ) it will connect to a spare HDMI port on the TV, then all sound is directed to the DTS optically....The neighbours may get restless
I have two Jamboxes. Love them. Portable, good battery life (about 10 hours), good sound, easy interface, pair easily via Bluetooth. They usually sell for about $180-$200. I've seen them as low as $140 at various times.