My preference has always been to take 80/94 to 355 (which becomes 290). It avoids 90 through the city, and 294. It's a few miles longer but the odds of getting into a major mess are much less. From the Indiana line on 80/94 I can get to 90 (via 355) in exactly 1 hour almost every time.
I do always leave the 294 option for a last minute traffic map check as we get close. If 294 is all green, and I'm feeling lucky, I'll give it a try. Though, even best case the junction of 294 & 290 is always a back-up (even as I look at it right now).
There's construction on 90 around O'Hare out to 290, but it's not bad (outside of rush hour). Once you get past 290 it's smooth sailing until WI. There are a couple of shoulder limitations under bridges on 90 around Huntley (30 minutes past 290). They're more tap-the-brakes then congestion.
There is a Love's just past Interstate 65 before getting into IL that is RV convenient, has a dump station, water and propane (should you need it). And, it has IN gas prices.
Hopefully that helps!