Ah, the old question. You have a Chromebook, but you are also an Apple user and want to access your iTunes library on your shiny new Chrome OS devices. Unfortunately, Apple has yet to release – and probably never will – an Android version of iTunes. Many users have switched to Apple Music and are using the Play Store version or just browsing to Apple Music on the web. However, many have an extensive iTunes library and still others regularly use the Storefront for media shopping and consumption. Wouldn’t it be nice if you could do that on your Chromebook?
Well, where there is a will, there is a way and that way is through the Linux container on Chrome OS. Obviously, Apple has its own iTunes apps for iOS and macOS, but the company also has a Windows version of iTunes and that’s the path we’ll take to get the app on our Chromebook. First, you need to make sure your Chromebook supports Linux apps. To do this, simply go to the Chrome OS settings menu in the system tray. Click on the gear icon and in the settings menu click on Advanced. Click on “Developers” and select the “Activate” button to install the Linux environment.
Configuring Linux on Chrome OS
The first time you activate Linux on your Chromebook, you’ll be prompted to set a username and select how much storage you want to allocate for Linux. Keep in mind that the amount of storage you give Linux will be taken from the Chrome OS side. If you have a device with little storage, you’ll want to keep that amount just enough to install the Linux apps you use. (Don’t worry, you can adjust the amount of allocated storage later if needed.) I have half a terabyte so I set mine to around 200 GB. Your username, by default, will be the same as your default Chromebook login without @gmail at the end. You can do what you want with it, but remember what you are using because we will need it later for installing iTunes. Let this process take its course and when completed, the Linux terminal will appear and we are ready for the next steps.
Now that Linux is installed, we need to make sure that all of our packages are up to date. This can be done in your newly launched Linux terminal. If you accidentally closed it, you can find the Terminal app in your app launcher. Just click on the icon and wait for the terminal to open. In Terminal, paste or type the following commands and press Enter. (To paste, just copy the text and right click anywhere in the terminal.
sudo apt update && sudo apt upgrade -y
To run the Windows version of iTunes on Chrome OS, we will need the 32-bit version of iTunes which can be downloaded here. To run a Windows executable file on Linux, we will need to install a compatibility layer. In this case, we’ll be using the popular Wine package for Linux. Do not worry. The steps are relatively straightforward and if something goes wrong the Linux container can easily be removed and we can start over. Once you’ve downloaded the iTunes installer file, open your Files app and move it to the Linux folder. You can rename the file if you want but by default it will look like this: iTunesConfiguration.Exe. We are now ready to begin the iTunes installation process.
First, you will need to install the Wine Linux package and then add the 32-bit architecture to your Linux container. To do this, run the following commands in your Linux terminal, one at a time.
sudo apt-get install wine sudo dpkg --add-architecture i386
Next, we need to update all new packages and install the 32 bit version of Wine so that it works with our version of iTunes. Run these two commands, one at a time, in your Linux terminal.
sudo apt update sudo apt-get install wine32
Run the iTunes installation
Now that Wine is installed and ready to go, we’ll use the compatibility app to run the iTunes installer file. To do this, run the following command in your Linux terminal, replacing “username” with your actual Linux username that you configured when activating Linux. Use the two commands below, one at a time. If you renamed the iTunes installer file, don’t forget to edit it in the command with your username. During setup, you will be prompted to indicate that “AutoPlay” is not enabled. Click yes to activate this feature.
sudo apt update WINEARCH=win32 WINEPREFIX=/home/username/.wine32/ wine iTunesSetup.exe
iTunes is now installed on your Chromebook and the app icon should be in your app launcher. However, the execution path of the iTunes.exe file requires some adjustment before Wine can launch the application. To do this, we need to edit the iTunes.destkop file. You can find it by opening the Linux folder in your Files app. Click on the three-dot menu at the top right and select the option “show hidden files”. Now click on the following folders to find the iTunes.desktop file.
Local> share> apps> wine> Programs> iTunes. Right click on the iTunes.desktop file and select “Open with Text” to open it in the text editor. Line three should contain an Exec command. Replace entire line three (3) with the following text and save the file. Remember to replace “username” with your Linux username.
Exec=env WINEPREFIX="/home/username/.wine32" wine "/home/username/.wine32/drive_c/Program Files/iTunes/iTunes.exe"
Launch iTunes on your Chromebook
You are now ready to run iTunes on your Chromebook. Clicking on the app icon in the app launcher will launch iTunes and you can sign in with your Apple ID to access the store and your library. I received a warning that my connection might not be secure, but you can click Continue and ignore the warning. Speaking of warnings, this is not a nice solution. I am using an 11th gen Chromebook Core i7 with 16GB RAM and iTunes is still freezing my device because it goes through so many layers and it is not technically designed for Linux. Still, it works and it’s a viable option if you need to access your iTunes library in the blink of an eye. Personally, I would recommend switching to Apple Music or YouTube Music, as iTunes feels more and more dated over time.