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Wine is a compatibility layer capable of running Windows software within a UNIX system, e.g. MacOS, Ubuntu, Fedora, and other Linux distributions. Wine is a free open source program that can be installed and run a large and ever growing amount of Windows software. It requires a good degree of technical knowledge but is 100% free.
Crossover is a commercial application of Wine made by a company called Codeweavers designed to simplify the process of using Wine. It runs like an application and in the event you need help offers support for a fee if you need help. Of the paid options, Crossover is the least expensive. Additionally they also offer versions specifically designed for use on Linux in the event you would like to run Windows programs on your Linux machine.
VirtualBox
VirtualBox is an open source virtualization program offered by Oracle. It will virtualize multiple OSes on Windows, Mac, and Linux. In addition to virtualizing an OS, VirtualBox also let's you virtualize hardware. This means that if you want to run an older version of an OS that is not supported by your current hardware, you can virtualize the older hardware to run the OS.
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