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I used to live in Chicago area, and attended school in northern Indiana. I found that it was usually better to take I-294 (the bypass) than to take I-94 (downtown). Even though it's a bit longer on the map, it seemed to keep moving with the additional lanes available. Whenever I go back to Indiana, I still take the I-294 tollway. It's also helpful to purchase an I-PASS. You can get these at Jewel-Osco stores in Illinois (there's probably other places to get them too, but I'm a bit rusty on that part). The I-PASS lets you use the fast lanes on the tollway, and cuts the cost in HALF. The website for more of that info is: Tolls and I-PASS - www.illinoistollway.com. It doesn't expire, and you can manage the account online after you have the device.
I would have to agree with Pat! My sister in law lives down in Indiana and that is exactly how all of us use to get back and forth. It goes so much faster!!
I go through that way several times a year visiting family back in Ohio. Sometimes I go right through downtown. Sometimes I go around. I tend to listen to AM 780 about 45 minutes out of town so that I can start to see what traffic is like and which way to go. If you have Satellite radio, Sirius has a Chicago traffic and weather station that also helps. However, the best bet still is to avoid rush hour if possible and be flexible. Tuesday I was coming back from Ohio and had planned on going 294. But, due to the storm, there were numerous wrecks, so I plowed through downtown.