yes, pretty easily too

you even have enough mileage to connect through lot and Warsaw on the dream liner. some fuel surcharge but much less compared to Lufthansa or air Canada

Winnipeg to Chicago to Warsaw to Prague stop to Zurich to Rome on the way there, and Rome to Zurich to Amsterdam stop to Chicago to Winnipeg on the way back is mpm 5 on the way there and mpm 0 on the way back, while avoiding surcharges except lot