列の結果のペアでgroupをクエリ

左結合でそれを行い、2つの日付を引くことができます：

select 
  t.id, 
  t.action_date login_date, tt.action_date logout_date,
  t.user_id,
  (tt.action_date - t.action_date) / 100 session_time
from (
  select * from session where status = 'LOGIN'  
) t left join (
  select * from session where status = 'LOGOUT'    
) tt on tt.user_id = t.user_id and 
  tt.action_date = (
    select min(action_date) from session
    where status = 'LOGOUT' and user_id = t.user_id and action_date > t.action_date
  )

デモ をご覧ください。 。
結果：

| id  | login_date          | user_id | logout_date         | session_time |
| --- | ------------------- | ------- | ------------------- | ------------ |
| 1   | 2019-07-16 07:06:55 | Bob     | 2019-07-16 07:29:13 | 22.58        |
| 3   | 2019-07-16 07:30:31 | Bob     | 2019-07-16 07:49:50 | 19.19        |
| 5   | 2019-07-16 08:05:55 | Tom     | 2019-07-16 08:15:13 | 9.58         |
| 7   | 2019-07-16 09:13:55 | John    | 2019-07-16 09:20:13 | 6.58         |