Do you mean you are using webmail inside Chrome, or do you use another email client e.g. Outlook?
If Outlook, possibly the file where they are stored is corrupt. You can recreate it and add your contacts fairly easily (though you can't readily add people not in your contacts, and of course there may be another cause). Though you can save the file where they are kept before you try to correct it, so that you can restore it afterwards if it doesn't work as hoped.
If you want to try this - open File Explorer, and put %LOCALAPPDATA%MicrosoftOutlook in the address bar and press enter. You'll then see a folder called RoamCache. Rename that to OldRoamCache.
Start Outlook (which recreates that folder), open a new mail and in the To field add all the emails addresses you want in the file (All of them maybe!). You don't need to send the email. I think this adds them to the file. (If it doesn't just rename the OldRoamCache folder back)
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