1. Open iTunes.
2. Click on the Music tab in the top left corner of the window.
3. Select the songs you want to shuffle.
4. Click the "Shuffle" button (the circular arrow icon) in the bottom left corner of the window. The selected songs will then play in a random order.
5. To stop shuffling, click the "Shuffle" button again.
To shuffle songs on iTunes using a Windows PC:
1. Open iTunes.
2. Click on the "Music" tab in the top left corner of the window.
3. Right-click on the songs you want to shuffle and select "Shuffle" from the context menu.
4. To stop shuffling, right-click on any song and select "Stop Shuffle."