I am based in YYZ but booked ORD-YYZ-HKG on AC due to much cheaper price. I booked another one-way YYZ-ORD to "catch" my outbound flight and for my inbound flight I will just ditch my final leg to ORD.

I'm planning to upgrade my outbound and the exact itinerary is as follow:

Sep 28 - morning - YYZ-ORD (on Porter, actually to Midway Airport)
Sep 28 - evening - ORD-YYZ (beginning of the above-mentioned AC itinerary)
Sep 29 - morning - YYZ-HKG

So I will basically have a day trip in Chicago before heading to HKG. I will head back home to sleep the same night. The baggages that will come with me to HKG will only be checked in on Sep 29 before boarding AC15.

It's a bit complicated and my questions are:

1. If I surrender my SSWU at ORD (and have them issue the boarding pass for AC15), can I re-check in my baggages the next day at YYZ?

2. If the answer is no for question 1, do you know if I can just upgrade YYZ-HKG but not ORD-YYZ (if that solves that problem)?


Thanks a lot!