It's almost impossible to find a mechanical chronograph for under $1000 that's in ready-to-wear condition.
If you need a good-looking mechanical watch on a bracelet, I'd recommend the Stowa Seatime. Not a chrono, but it's very well-made, unique and retains its value. There's a waiting time for new ones (I think two months now and about $900 shipped), but used ones pop up every so often on Timezone or Watchuseek. You can score one for less than $700 if you're lucky.