Can you give me the best route through Chicago?

I will be driving through Chicago, coming from the south on I57 and then continue further north up toward Milwaukee on I94. I will be driving an SUV pulling an open trailer, the trailer has a small sportscar on it. I only describe what I am driving because older interstates sometimes have very tight lanes.

I looked at a map and saw there is a tollway (294) but I was not clear if it is for local people who have electronic passes and possibly you cannot get on with cash? And, when I looked at the Tollway website, there are actually fees for larger vehicles, I don’t know what I classify as? I think of varied pricing as a turnpike not a tollway, so I am unfamiliar with the set up.

Otherwise it looks like taking I94 through downtown is the best direct route, but of course I am concerned about traffic. We will get to Chicago area around 2:00 I think, so should be good for missing lunch traffic or rush hour.