Yeah, you should file 2 flight plans to avoid any confusion or at a minimum put in the remarks you want instrument approaches at JVL. We get Mx flights at ORD alot that do round robins.....they file weird stuff like ORD..JOT..ORD. Not happening that way. We usually ask the pilot as they taxi out what there intentions are. Some literally want to just fly a pattern. Fine, coordinate it with C90 and as long as there aren't major delay issues they are gone. If i were you I would file to JVL with remarks of multiple instrument approaches. Have the JVL DPA filed as well and pick that one up once you are done doing your practice approaches. Bottom line....JVL and other nearby airports are handled as tower enroutes most the time. You can expect to be radar vectored the majority of the way. If your flight plan showed DPA as origin and Dest.....then you may confuse the controller becuase they aren't going to see everything you requested unless you put something in the remarks sections.
as for clarification on your route, re examine what you've been taught. Just cause you filed it doesn't mean your gonna get it. If you get a clearence of cleared to lets say JVL via Radar vectors....they aren't radar vectoring you to your victor airway, its to the airport. if you were cleared to JVL via heading 270 expect radar vectors to Nuelg then as filed.....then its vectors to the fix then you fly your filed route. Get what you've been taught out of your head, it will get you in trouble later on. If you don't hear "Then as filed" you aren't going to do anything you filed. If i were you, i'd call DPA tower, get the standard routes and altitudes they use to the nearby airports, or get prefered routes from the AFD, cause more then likely you'll get those. Don't ever expect to do what you filed. When i flew corporate back in the day. I just filed direct for everything unless I knew i wasn't going to get it.