Thank you all for your help. I have sent the split ticket scenario that Fermat found to my TA. I found out today that the TA is new to the company, so am planning to take her to lunch so she better knows my travel preferences. And while I am expensing the trip, I have a finite budget and still have to watch my pennies. I have also asked the TA to try scenarios out of ORD as E+ on UA should make the 7+ hours easier.
I'll let you know how it goes.
Thanks again,
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I miss Canadian Airlines