This tutorial covers everything you need to know about sideloading iTunes on Chromebooks. All you need is your Chromebook and an internet connection.
Installing iTunes on Chromebooks: What You Should Know
The 64-bit version of iTunes (for Windows) doesn’t work on Chromebooks. Likewise, not all versions of the 32-bit iTunes work properly in ChromeOS. We installed the latest 32-bit iTunes (v12.10.11) on our test device, but the app was unusable—it crashed every time. Our research revealed that other Chromebook users had the same experience. iTunes v12.9.3 (32-bit) was more stable, but it’s no longer available for download on Apple’s website—most likely because it’s an outdated version. However, you can download that specific iTunes version from third-party software download sites for Windows. Save the iTunes executable file in your Chromebook’s Linux folder. For this tutorial, we saved the setup file as iTunesSetup.exe. Note: Although the iTunes version works, some features and functionalities might be unavailable. Also, the app version may malfunction because it’s retired and outdated.
Set Up Your Chromebook’s Linux Development Environment
ChromeOS Linux development environment supports Chromebooks running ChromeOS 69 or newer. Jump to the next section if the Linux development environment is already set up on your Chromebook. Otherwise, update your Chromebook’s operating system (Settings > About ChromeOS) and follow the steps below to enable Linux support in ChromeOS.
- Head to Settings > Developers > Linux development environment (Beta) and select Turn on.
- Select Next to proceed.
- Enter a preferred name in the “Username” dialog box or use the system-generated username. In addition, use the Recommended disk size and select Install to proceed. ChromeOS will download the files needed to set up the Linux environment. The operation takes a couple of minutes, depending on your connection speed and Chromebook’s hardware configuration.
Install iTunes on Your Chromebook
Wine is a virtual emulator that allows you to run Windows apps in your Chromebook’s Linux development environment. Follow the steps below to set up Wine and use the emulator to install iTunes (for Windows) on your Chromebook. Ensure your Chromebook has an internet connection. Otherwise, you may encounter several error messages while setting up iTunes. sudo apt-get install wine This command installs Wine Linux in the Linux environment. Since you’re installing the 32-bit version of iTunes, run the next command to set up Wine’s 32-bit architecture. That allows Wine to install 32-bit apps without issues. sudo dpkg –add-architecture i386 WINEARCH=win32 WINEPREFIX=/home/username/.wine32/ wine iTunesSetup.exe NOTE: Replace “username” in the code with the username of your Linux development environment. The text before “@penguin” at the top of the Terminal window is your Linux username. Also, replace “iTunesSetup.exe” if you saved the iTunes executable file under a different name. One final thing you need to do: modify the iTunes desktop file so your Chromebook can run the app. Opening iTunes without doing this will trigger a “Path Not Found” error. You should see an Exec command on the third row. Exec=env WINEPREFIX=”/home/username/.wine32″ wine “/home/username/.wine32/drive_c/Program Files/iTunes/iTunes.exe” Replace “username” in the command with your Linux username. Likewise, replace “iTunesSetup.exe” if the iTunes executable file has a different name on your Chromebook. Check the “Linux apps” folder if you don’t find the iTunes app in the central app drawer.
Apple Music Also Works
If iTunes doesn’t work, use the Apple Music app for Android to access your iTunes music library. The Apple Music app is available in the Google Play Store for Chromebooks. The app is stable and has a similar interface as the Apple Music app for iPhone and iPad.
