If I were spending that range of $ on a chrono, I would consider
http://www.westcoastime.com/ow77chronpil.html
which is modeled after a Heuer bundeswehr pilots' chrono.
If spending more, I would lean toward an actual vintage Heuer
http://www.vintageheuer.com/heuerwatchesframeset.htm
But watches are all about personal taste - heck, $20 at Target will get you a perfectly good timekeeper - so buy what you want.