I have flights booked on 29Apr as follows: "hellhole where I live" to YYZ on AC arriving at 13:38 hrs CO3307 YYZ-EWR SCHEDULED to depart 17:40 arrive 19:27 CO2338 EWE-RIC SCHEDULED to depart 21:41 arrive 22:59 These are award tickets, and was the only routing I could get for the day I needed. When I booked them it all looked good -- lots of time to kill in YYZ but have MLL access, so not a huge problem. Also didn't mind the 2 hrs in EWR since I've never been there, gave me some time to have dinner and look around the airport. THEN, I started looking at the past history of CO3307 and CO2338. It does not appear that either of these flights actually take off anywhere near the scheduled time. According to FlightStats CO3307 is on time only 42% of the time with an average delay of 84 minutes. CO2338 is only on time 56% of the time with an average 75 min delay. Today already early in the morning they are forecasting nearly a 3 hour delay for CO3307. What's up with that? How can they already know it's going to be a 3 hour delay, especially when they're showing the previous flight for this aircraft today as on time? My real concern is missing the connection with CO2338 since by the time I might miss the connection, I will already have paid for my hotel room in Richmond for the night. It looks like CO2338 usually goes off late as well, but it would be just my luck that this would be the one time that flight goes out on time. Observations, advice, or any kind of "what the heck is up with that" explanation? This is the first time I've ever flown CO - most of my flying has been AC & United.