I estimate that I will have 45 minutes between arriving at O'Hare and when my flight leaves. I will have two bags to check in, and I'm on an international flight with EVA Air that leaves at 12:30 AM. Will 45 mins be enough time for me to check my bags, go through security, and board the plane?
Question update: What if, in a different scenario, I have 1 hour 30 minutes between arriving at O'Hare and the flight's departure, also with 2 bags to check?
Below is a screenshot of the flight I intend to board.
Additional UPDATE: This is the full plan for my trip in the case where I expect to arrive 1hr30 mins before boarding:
Leave Ann Arbor 6:51pm, arrive at Chicago O'Hare at 10:25pm (see screenshot below) on Amtrak (this is the only transport (coaches considered) that's compatible with my schedule that day).
Pre-schedule an Uber to go from Chicago Union Station to O'Hare, taking around 35 mins (also see screenshot below). Hope to get there no later than 11:05 in the worst case scenario. I can have the Uber drive me straight to terminal 5, which is where EVA Air will be.
I appreciate all the answers and comments - they've really helped.