With OpenSSL, if you know you're going be chrooting, you can explicitly seed the internal PRNG with a call to RAND_poll() before you chroot, avoiding the need to open /dev/urandom once you've chrooted. (Similarly, you're supposed to call RAND_poll() to re-seed after forking because there's no safe way to detect that you've forked. Of course, if you fork while in a chroot you're screwed.)
I really think that LibreSSL's RAND_poll() should have similar behavior to ensure maximum compatibility with OpenSSL and to provide a means to use chroot() safely without the risk of falling back to the "bobo" code. (Also, a means of safely reseeding after a fork on systems without minherit(MAP_INHERIT_ZERO)).
(Incidentally, libsodium has a similar API: you can explicitly call randombytes_stir() to cause the library to open (and keep open) a file descriptor to /dev/urandom, so subsequent calls to the PRNG work in a chroot.)