If all is working as advertised, should be pretty fast, depending on data connections.
From:
http://support.apple.com/kb/HT4486?viewlocale=en_US&locale=en_US
=====
When you enable My Photo Stream on your devices, all new photos you take or import to those devices will be automatically added to your photo stream.
iOS devices: New photos you take are automatically uploaded to your photo stream when you leave the Camera app and are connected to Wi-Fi. My Photo Stream does not push photos over cellular connections.
Macs: Any new photos you import to iPhoto or Aperture begin uploading automatically when you have a Wi-Fi or Ethernet connection. Or you can change your iPhoto or Aperture preferences so that only photos you manually add to My Photo Stream are uploaded.
PC with iCloud Control Panel 2.0 or later: Open a Windows Explorer window and under Favorites select iCloud Photos if you are using iCloud Control Panel 3.0 (or Photo Stream if you are using 2.0 to 2.1.2). Open My Photo Stream. Click the "Add photos" button. Select the photos to import to My Photo Stream, then click Open.