HTTPS redirect from custom port to port 443

The problem is that you're doing HTTPS at the 8443 VIP but you don't have a client SSL profile. You need that to decrypt the client's SSL and process the underlying HTTP request.

"[HTTP::jiratest.chicago.xxx.com]" isn't valid. You can explicitly name the URL:

HTTP_REQUEST { 
    HTTP::respond 302 Location "https://jiratest.chicago.xxx.com" 
}

Or you can use [HTTP::host] to redirect back to the FQDN that the client requested

HTTP_REQUEST { 
    HTTP::respond 302 Location "https://[HTTP::host]" 
}