I promise I'll work Amtrak into this post so bear with me.
Mr. buddah, have you considered a more conventional approach to air travel? You are one of probably the only persons in your town to take that route to O'Hare and without doubt it has to be the longest possible way to get there. That said, let me tell you of my last air travel experience and the timing needed.
Left home for CLE at 9:12 AM (later than originally planned by about 10 minutes).
Parked at remote lot and took bus to terminal arriving about 9:55 AM.
No line at security so just a few moments to clear that step.
Arrived at the gate at probably 10:05 AM for a 10:55 AM flight to LGA.
Boarded and backed out about 5 minutes early.
Big tailwind, no ATC delays into LGA.
Parked at gate at about noon (30 to 35 minutes early).
Doing this well, decided to have lunch at the LGA food court (multiple selections there).
Board shuttle bus to rental lot and leave rental lot about 12:45 or 12:50 PM.
Navigate my way over to New Jersey through relatively light to moderate NYC traffic (didn't fly to Newark as it far more expensive).
Arrived at Metropark station at 1:50 PM.
Picked up co-worker who arrived Metropark on Acela 2164 a few minutes earlier than scheduled 2:16 PM. Had convinced co-worker to take train there from the south as it was drop-dead simple.
Total time from home in Ohio to Metropark was 4 hours and 40 minutes via LGA and stopping for lunch. Would have been less via EWR had I done that route. Granted, this was as good as it can possibly get and it can be far worse getting into the New York area in bad weather. OTOH, it's hardly the torturous experience that you make it out to appear.