If you have a couple minutes to spare, it's worth a quick once around the block to see if you can find either a meter spot or a 15 minute standing zone (NOTE: NOT a loading zone, a STANDING zone, you can leave your car with the flashers in the standing zone and not be in it, loading you'd better be there). Meters are expensive, but still cheaper than the lot.
WBBM AM 780, traffic and weather together on the 8's. Note that our traffic reports are by name, not number.
I-90 is the Indiana Toll Road (in IN), then the Skyway (state line to merge with 94), then the Dan Ryan (with 94 to downtown)
I-94 is the Borman (in IN), then the Kingery (state line to split from 80), then the Bishop Ford (split with 80 to merge with 57) then the Dan Ryan (57 merge to downtown, including the merge with 90)
clear as mud, right?
On an "average" day, late morning, there won't be a whole lot to worry about until you're really close to the city, so you're going to be listening for accidents on any of the above.
construction notes:
1. The ramp from 90/94 to east 290 is closed due to construction. Google Maps seems to know about this and wouldn't let me force the route to that ramp, if you're using a GPS or other map program, make sure it's not asking you to exit onto east 290. google said to exit at roosevelt, go east to canal, then north on canal to union, which seems reasonable to me, but I don't drive in that area very often, so if anyone else knows the area well and that stinks, please chime in
2. Avoid going east of Canal (ie crossing the river), as Wacker is closed from Jackson to Madison and the bridges on Monroe and Adams are closed. so, if you go across the river, you can end up needing to go around quite a few blocks to get back.