You can send files of any size with Skype's Send Files feature.
Want to send a file to the person you're talking with? No problem - just click on the Send File icon and you'll be able to browse within your files for the one you want to send.
Skype gives you multiple file sending options:
- You can send multiple files at the same time.
- Drag and drop a file to a name in your contact list; the person must be online in order to recieve the file.
- If you're in a chat and would like everyone to receive the same file, just click on the "Send File To All Participants" button.