The best way to go through Chicago, is to not go through Chicago.
From Indy, take I-74 west to Bloomington and pick up I-39 North (74 will dump you onto I-55 North at Bloomington, the 39 exit is one mile past where 74 splits back off). Take I-39 north into WI (it'll join up with 90 near Rockford and 94 near Madison). At Madison, take exit 135 to US 151 North. *After* you pass Waupun, take WI-26 North. (26 crosses 151 both before and after Waupun, you want the 2nd one. First will work, but you'll be a bit slower going through town.) 26 is 2-3 lane (passing lanes every few miles) but only goes through one small town. 26 will cross US 41 and you're there (the folks coming up 41 from Chicago will be exiting onto 26 to get into the show, so there'll be lots of signs and such.)
The above is around 50-60 miles farther than going up 65 through Chicago, but it's worth every last one of them.
As far as other routes: 74 to 57 takes you quite a bit out of the way and you don't really skip Chicago at all, just I-80/94. 57 also has no exit onto 294, so you're likely to end up on the Dan Ryan.
Whatever you do, you do NOT want to end up on the Dan Ryan! (94 from the 57 split up to downtown). It's all torn up and is a mess and you'll regret it.
If you want to chance Chicago (and those folks coming from the East, ie not going through Indy, almost have to), take 294. You'll hit 5 tolls between Indiana and Wisconsin, but it's only 3 miles longer than taking 94 straight through downtown and you won't have to worry about the Dan Ryan. Also, the best time of day to do this is between 8 and 10 PM. The afternoon rush hour should be pretty much done by 8, but at 10 they set up the overnight road work and mess things all back up again.
Also, note that none of the above (except skipping the entire Chicago area via 74/39/151) works 100% of the time. It's best to either use Google Maps on your cell phone with Traffic turned on, or listen to AM 780 for their "traffic and weather together on the 8's"
08, :18, :28 etc.) and see what's really going on. They go through traffic on the radio REALLY FAST (that's what ORD controllers do after they retire
), so here's the ones you really need to listen for:
* The route around on 294 will be covered by just "80/94" and "the Tri-State."
* The route through town is "80/94," "the (Bishop) Ford," "the (Dan) Ryan," "the Kennedy" (only "out to Montrose" or "to the split"), and "the Edens."
They won't give you a time going around, but unless there's at least 2 backups northbound it's probably running fairly smooth. The through-town route, you'll want 15 minutes or less for the Ford and the Ryan (hah), 20 or less for the Kennedy and the Edens.
Hopefully this will show you that the best way to get through/around Chicago is to fly.
Last year I took 90/94 going up and 294 coming back. Both ways was pretty scary.
