Given 290 EB between Wolf and Austin at any time of moderate traffic, that could be a rather close call time-wise. If you were going to do that, you'd want to approach it from the north, probably Mannheim - Irving Park - River - (stop at Gene N Judes for a hot dog if traffic has been light) - First - Madison - Des Plaines. Not something I'd recommend to somebody who isn't familiar with the area.