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With regular find-file it's possible to supply *.[ch] to open all .c or .h files in a directory. ido-find-file doesn't seem to support this behavior.
I know I can press C-f while ido-find-file is open to switch back to regular find-file, but is there a way to tell ido that I always want to use the regular expression matching?
Help says that C-t toggles regular expression matching, but it doesn't seem to have any affect to me.
Ido cannot select multiple items. You'll have to use the normal find-file or Helm.
On the Emacs wiki there seems to be a gist for multi selecting items in Ido but I'm not sure if it works: http://www.emacswiki.org/InteractivelyDoThings
ido-toggle-regexp does work. The problem is that it only allows using regexps to filter candidates, not selecting multiple candidates.
Nov 18, 2014 at 16:53
o.*g or org$ in my directory of org files nothing appears.
default-directory full of .c and .h files, try pressing C-x C-f C-t [ c h ] $ (key presses are separated by spaces here). Once you're done typing ido will filter out candidates that don't match. Note that it uses regexps and not globbing. Now press C-t and it should say "No matches" (assuming that you don't have files with that strange name).
Nov 18, 2014 at 17:00
helm-projectile-find-file. Here is a demo: as you see, I opened all marked files and later using 
helm-mini to show all available buffers that were created from multiple-file opening. You can also do the same thing with helm-find-files, except for the current directory only (since helm-find-files is a replacement for stock find-file).
C-x C-f *.[ch] RETyou are not using a regexp. You are using a file globbing pattern (see the shell). And this pattern-matching is only forRET, not for completion. If you want to use regexps for pattern-matching for completion, try Icicles.