Since the TAF is only valid for a 5-mile radius around ORD, and PWK is 13 miles away, you can't use the ORD TAF to determine that you don't need an alternate for PWK. However, because the FA is valid for PWK, your "guys" are legal launching to PWK without an alternate if the FA shows 2000-3 or better +/-1 hour.
That said, if the FA says 3000-5, and the ORD TAF says 300-1/2, I'd be hauling some extra gas on my run to PWK even if the FAA doesn't say I have to. Ditto going into ORD with the TAF saying 3000-5 and the FA saying 300-1/2. Consider it my conservative nature. :wink2: