Errr… this is a sort of “six of one, half dozen of another” question.
The most direct route (ha-ha) is the Damn Ryan. On the bright side, during rush hour it is difficult to get into a high speed collision on that road - running out of gas because you’ve been at a stand-still is more likely.
The 294 route is longer, and at rush hour almost as crowded.
If it was me, personally, I’d hang out at Midway for some hours before heading north. But then, I’m nutty about airplanes.
There is the train route - either the Orange line to Wabash (elevated line) and transfer to the Red line on State Stree a block west (subway), then north to Howard and so forth… or take the Orange line into the loop and catch a Metra train going to Glenview. Longer time, yes, but no driving. On the other hand, rush hour trains are not much fun either. And you wouldn’t want your aging parents going that route as standees.
OR - there are shuttle busses that run from the airports to various suburbs (Tri-State is the one I’m famillar with). They could take a shuttle from Midway to points north, thereby letting someone else do the heavy driving through town. Much more comfortable than the CTA/RTA/Metra, although it will cost a little more too.
You know, I feel so bad about your folks having to drive the Damn Ryan in rush hour I almost want to pick 'em up at Midway myself and fly 'em to the north suburbs. Which is the expensive option - it is theoretically possible to have a small plane pick them up at Midway and fly them to the north suburbs, like Palwaukee or Waukegan and travel by car the rest of their trip (I’m assuming they’re renting) Depends on good weather, of course. A crazy idea, but it would be a memorable part of the trip. Wouldn’t take very long, either, since there’s no chance you’d be stopped in traffic.