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Traveling through Chicago?


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I am traveling from Ohio to Madison, WI and I will have to drive through Chicago. I have never been to, or been around, Chicago so I don't know what to expect. I looked on MapQuest and it said I would be on I-90 through Chicago, but it mentioned all of these I-90 Express and stuff like that. Are there a lot of signs on the interstate for I-90? I don't want to get lost, and I am not used to driving so far alone. Are the signs on the interstate pretty straight-forward and easy, or will I have to pay close attention to make sure I am on I-90 W Express and not just I-90 W. Sorry if this is a stupid question, any help is appreciated.

Travel Tips
OK most of the above answers are confusing.

I work for a Chicago area messenger/delivery service and have driven extensively in the area. I also go to Wisconsin, North of Madison almost every weekend....here is what to do and at the end is what not to do:

At the IL/IN border follow 80/94 to I-294 North marked Milwaukee. If you cannot hit the IL border by 6:30AM CDT, you are better off after 9AM but before 2PM. Follow 294 to 290 West which is marked Rockford. Stay with the Rockford signs for about 18 miles. There will be an Exit for I-90 West...also marked Rockford. Get on I-90 West and it will take you to Madison. Depending on traffic, you will be about 2 hours from Madison after you merge onto I-90. Most of these roads are tollways and the tolls vary. Stay to the right since you will be paying cash (lavender lane signs).

DO NOT.....under any circumstances attempt to take the skyway or I90/94 aka Dan Ryan as you cross the border from Indiana. The construction is world class, the backups are a nightmare at anytime of the day or night. This is a 12 lane highway currently operating at 4-6 lanes. It is all trucks and construction vehicles.Nobody in their right mind drives on it now much less a visitor.

Have fun, it's not as complicated as it may sound!
Others
You know what you should do. You should just buy tickets at www.YTBtravelWorldPro.com so that you won't be lost in your next vacation.
www.YTBTravelWorldPro.com
to be honest with you, i'd avoid chicago. :) i guess it really depends on what time you will be driving on i90 since it's a pretty busy highway, especially during rush hour. you should print out some directions on mapquest and also be attentive with the signs. if you get lost, people are pretty helpful if you ask for help. hope that helps and good luck! :)
Don't listen to the first two posts...how dare they. Road trips are fantastic and if you don't mind a bit of traffic driving through Chicago is an Awesome experience. Sure its a bit crowded once you get to the South Side, but the view is amazing. Chi-town is one of the most beautiful cities in the US.

OH yeah, there will be no issues with getting lost - there are plenty of signs to point you in the right direction. The Kennedy expressway is a big freeway and offer a lot to look at on the drive through.

Enjoy!!!!!!!!!!!!!!!!!!!!!!!!!...
Born and raised in Chicago - My entire family (except me) is still there.
Take the I80/94 around the south of the city to I294 and avoid the city. Take I294 to I90 toward Rockford. These are tollways however.

The south side expressway is under construction and is a mess. It is shorter but may add 1-2 hours to your trip during the day. If you do want to see the city and drive through it, take the Dan Ryan to the Kennedy Expy and that connects to I-90
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