Certain websites keep logging me out (Chrome)
Solution 1:
It is possible that your cookies are corrupt. It are cookies where the login information is stored. If this is corrupt, it may not update properly, and thus the expiration date is set to a date in the past, which effectively means that every time you login, the cookie is expired and it requests you to login again.
To solve this problem, clear your cookies. This will log you out of every site though, but once you login again, it should stay.
Solution 2:
In my experience, many websites don't manage correctly the "Remember me" option. This happens even with some very large companies that I use, where this option never works in their websites, no matter which browser or platform that I use. Unfortunately, a large company does not always have the best website or employs the best developers.
It's also my suspicion that for some websites the "Remember me" checkbox actually does nothing.
I recommend using a cloud service for keeping your logins, for example Bitwarden or its alternatives.
A password manager, especially cross-platform one, can much simplify the repetitive logon to such badly-programmed websites.