John,
For the Geneva race (at least) don't bother with the expressway. Get to Lake Geneva and take 120 South (use the bypass as it will be a Saturday). It turns in to Il 47. Taking that south will offer about 10 ways to cut over into the area. The Expressway is quicker when it's quicker... but not by a whole lot. And when the expressway is not absolutely butter, it's a lot slower.
For Richton Park and Homewood (possibly even Willow Springs) you might find it quicker to come down 53 and run into 355. 355 will run into 80 which is absolutely the easiest way to run into the Southern Suburbs. There was some construction on 355 last week, but it wasn't bad. And the section from 55 down to 80 is only about 3 years old and always moves well.