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Yes, the small USB-C does fit the Chromebook. It has been around 20 years since we've used a monitor. Since then it's always been Mac all in ones or laptops, so I can't say what sort of connections monitors have, but the cable works great for connecting to the TV. Be sure to go into settings on your Chromebook, advanced settings, display and then choose to mirror Chromebook. At least that's how it goes for mirroring on the TV.
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