My take
1 Should be able to pick up tickets at Amtrak Toronto but there is no advantage. Just pick up in Chicago.

2 There is a ticket/baggage check counter where you can get it all done Pick up ticket and check baggage (There is a disadvantage to picking up tickets early) There is also a first class lounge where you can leave your carry-ons until train time if you care to explore Chicago's downtown area

3 Union station has parking but it is a long trek from garage. Are you renting from Hertz? If so their car return is in the garage as well. There will be no roaming red caps in or near the garage. 2-3 trips will be necessary.

4 At destination luggage will be brought to station proper. A claim check WILL BE NECESSARY. If you do not claim pretty quickly it will be stored securely and available during Baggage hours.

5 There is very little soundproofing in the room and none in the wall adjacent to the hallway so you will be heard. My suggestion is to take a room at the end of the car not in the middle. PS You need to get the snoring checked it is a good indicator of sleep apnea which can be a life threatening condition.

I gather from your post that you know 3 pieces luggage free and $10 for the other 3. Do not go over 50 lbs each as they will not be accepted.


There is also a way to send 2 more pieces of luggage to destination for about $100 but it involves going to DEPEW