"How should I file a flight plan for a flight that is part VFR and part IFR? For example, I live near ORD and if I file IFR for an entire flight, I'll get sent very far from my route."- Pete
“If you can safely depart VFR and I emphasize safely, you can file an IFR flight plan specifying the departure point as an airport near where you would like to pick up the IFR clearance.
A pilot departing VFR must be aware of the position of the aircraft and the relative terrain and obstructions. Remember, that you as the pilot are responsible for your own terrain and obstruction clearance until reaching the MIA or Minimum IFR Altitude.
If you are unable to maintain terrain and obstruction clearance, then you must promptly advise the controller. The controller will ask your intentions if you are unable to climb in VFR conditions.
(Note: you must remain in VFR conditions until receipt of the IFR clearance)
Request the IFR clearance from the frequency depicted on the approach plate for the airport you selected if you are not already talking to ATC and receiving advisories.”