If you are willing until a few hours before the flight, you often can make a prediction of which side will be the inside of the aircraft on the approach, and for takeoff- if you can predict the runway, you can figure it out by reading the standard instrument departure procedure for the flight plan that was filed (usually on flightaware.com 2-6 hours before US flights). However, as others said it is very hard to predict which runway, as there are many details that affect it. Generally if the winds are less than 6-8 knots, the airport will be in a calm winds configuration, which varies by airport.
For example, at Boston Logan, calm winds is depart runway 09, arrive runway 04R, unless the aircraft is a propeller plane, in which case, they depart runway 04L. (Source: http://bostonartcc.net/document_library/sops/kbos.pdf).
It gets much easier though at airports with one major runway. So, at Washington National, if the winds are from the south, they will land runway 19, usually on the River Visual, if the winds are from the north, they will land and depart runway 01, which means they will turn left towards Arlington immediately after takeoff.
If you take all of this into account and get the right wind forecast, you can often choose what side to be on for landing, however, it is much harder in my experience for takeoff, because of how many departure options there are for takeoff.