Star Alliance - YUL-GRU under 1500$ in August

Gotta be in GRU Aug. 7-13 for work. I usually fly AC but I can't figure why they are 1750$ (750$ more than DL)! Want to stick on a *airline and open to some creative routing involving a positionning flight with AP miles. My company provides 1500 for airfare. Outside the time I have to be in GRU, my work schedule in flexible so I could combine some work/vacation before or after the trip. Any suggestion on a possible routing?

Gotta be in GRU Aug. 7-13 for work. I usually fly AC but I can't figure why they are 1750$ (750$ more than DL)! Want to stick on a *airline and open to some creative routing involving a positionning flight with AP miles. My company provides 1500 for airfare. Outside the time I have to be in GRU, my work schedule in flexible so I could combine some work/vacation before or after the trip. Any suggestion on a possible routing?

UA is $1489 via ORD on the outbound (15h24 arrive on 7th at 09:45) and EWR on the return (17h19 departs on 13th at 21:10)

JJ offers decent fares via ORD as well. Anyone could compare JJ inflight service & comfort vs UA? I flew internationally with both UA and CO a couple of times, TATL and EZE, but never flew on JJ...

Finally booked 2 flights YUL-YYZ-SCL RT for 1021 ai on AC in Y. And SCL-GRU for 324$ on JJ in Y. This way I get the max. miles (14 960 instead of +/- 10 500 on most YUL-GRU routes with 1 stop) and will be able to take a few days off in SCL!