Potential itinerary

Leave Friday from Ottawa to Aldershot (end of the line) - VIA train
Depart: 12:25 Arrive: 18:23
Cost: $78.75

Aldershot to Hamilton - GO Trian
20 minute commuter train
Cost: $3.70

One evening in beautiful Hamilton

Vanier Cup - Saturday at Ivor Wynne, 2pm kick off.

Limo from Hamilton to Toronto Airport - shared cost - $90 (we arrange ahead of time to have him pick us up about 5:30 at the stadium)

Leave Toronto to Montreal - Westjet flight
Depart: 16:45 Arrive: 19:57
Cost: $138.25

Cab from the airport to downtown to meet the guys - $30ish - shared cost

Saturday night on tour in Montreal, stay in the official Hotel Maritime, already booked

Sunday - Grey Cup

Return Monday from Montreal to Ottawa - VIA train (assuming that's how the other guys are going)
Cost is $34.99