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on the season 4 DVD there is a "prequel" that bridges Seaon 4 and Season 5 in which Chloe meets Jack in Chicago. Its like 10-15 minutes long and not really all that necessarily. I have anther post on it earlier in the thread

If you buy the DVD set for the last season they include a "bonus" disc that gives you a episode that is not shown on TV. I don't know how long it lasts, I think about 10 minutes but then I can't believe how fast an hour goes when you are watching.

This last bonus disc starts "12 months later". Jack is in Chicago,has long hair and kind of homeless looking. He meets Chloe who tells him somehow someone has unscrambled the telephone call to President Palmer and they know he is alive. That he has to get out of Chicago and get out now!
From the set it does look like it is set in Chicago, but regardless, Chloe obviously has flown from LA to Chicago to tell him to get out. Jack asks if Chloe has been followed, and she says in her matter-of-factly way, "No, I'm here".
Then as Chloe leaves a motorcycle guy starts stalking Jack down the street and then comes a car gunning for him. Jack steals a car and manages to lead the guys into a crash and ultimately gets away.

Seems that without this information you wouldn't know until Sunday night that anyone knew Jack was alive until 18 months later.