No
Ask the local employee if you are on board for the most accurate answer at the time
No just go to your next flight the crew will change your bags over to the next flight for you until you reach your destination
if you only have a layover at Ohare, i.e. you are just changing planes, you will NOT need to recheck your bag. It will be moved to your next flight for you. You won't see it until you arrive in Detroit where it will be waiting for you at baggage claim.
Depends where you go though customs. If Chicago then likely will have to grab bags
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