I have no problems using USB serial ports with Windows software running on Linux/WINE. One of the reasons I switched to Linux was one USB cable I have would work on Windows 7 but not on Windows 10.
You have to configure the serial port permissions in Linux. There are instructions for doing that on the Chirp web site.
If you are using WINE 2.8 or later you might have to configure the port settings in WINE or manually make a "registry" key. There are instructions for doing that on their web site at
https://wiki.winehq.org/index.php?title=Wine_User%27s_Guide&oldid=2519#S...
Versions before that only require making a link in the wine folder to the port.
Older versions of WINE before about 1.7 don't support all the RS-232 lines. This probably isn't an issue for radio programming cables that only use TXD and RXD lines but it is if you need the RTS, CTS, DTR, DSR lines to work properly.