Hello, and Welcome to the HP Support Community!
It's difficult to make a suggestion without knowing what exact model ChromeBook you are using.
Normally, older USB ports do not have the ability for Video Out. Newer ChromeBooks have HDMI out ports built into them.
I use an older HP ChromeBook, and the only way I can stream the desktop is using WiFi via the "Cast Screen" option.
WyreNut
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Former Expert in the PalmOS, WebOS, and Android sections of this Community Forum.
I am a Volunteer here, not employed by HP.