I've not tried it, but being that most Chromebooks are on the lower end spec wise, it's probably not going to work out well. You'd need at least 8GB of memory. Most Chromebooks seem to have 4GB. Google Pixelbook has 16GB of memory and 512GB of storage, which makes it the most powerful Chromebook I know of. Even at it's $1600 price it only has a 1.3GHz dual core cpu. At that price point there are much better options in my opinion. Unless there's some specific reason you need a Chromebook, I'd look elsewhere.
There is no way to install IB TWS, or almost any other software for that matter, on a standard Chromebook. That's how Google minimizes the possibility of viruses on a Chromebook. However, if you have a powerful enough Chromebook, you can bypass the ChromeOS and install ChromBuntu which is a derivation of Ubuntu specifically for Chromebooks. But if you are going to go to all that trouble, you might as well just get a Linux laptop.
TWS works absolutely fine on a 4GB machine. Using it on my secondary machine with Windows 10. Granted, you will not being doing many other things as TWS easily uses 1GB.
Oh, sorry, I see you're running Windows. That's not really relevant to this thread, I'm afraid, at least not until Chromebooks allow Windows, which may be soon, I hear, and obviates the need for a Linux workaround.
Where did you hear that Chromebooks may soon be running Windows? I am very skeptical about that. Google has been trying for years to get Chromebooks to run Android software, and they still can't get that released. Plus, why would Google even want Chromebooks to run Windows?