Redmine

You can use CKFinder to uploading images in CKEditor plugin.
Also you can browse images in CKEditor.

• Requirements and tested versions :
  - Redmine 1.3.0.stable (installed by Bitnami)
  - PHP Version 5.3.8 (installed automatically by Bitnami)
  - CKEditor 3.4.2 (Redmine CKEditor plugin, http://github.com/ebrahim/redmine_ckeditor, 0.0.6-ebrahim)
  - CKFinder : ckfinder_php_2.2.2.1

I didn't test in redmine v2.x, but it will work.
(* CKFinder is not free.)

0. Stop apache server

1. Copy unzipped CKFinder folder into
C:\Program Files\BitNami Redmine Stack\apache2\htdocs

2. Copy helper.rb file into
C:\Program Files\BitNami Redmine Stack\apps\redmine\vendor\plugins\redmine_ckeditor\lib\redmine_ckeditor\wiki_formatting

3. Copy config.php file into
C:\Program Files\BitNami Redmine Stack\apache2\htdocs\ckfinder

4. Restart apache server

• Reference
  - CKEditor integration with CKFinder
  : http://ckfinder.com/demo
  - Detailed desciption about "CKEditor can be easily integrated with an external file browser/uploader."
  : http://docs.cksource.com/CKEditor_3.x/Developers_Guide/File_Browser_%28Uploader%29