We want to take a road trip beginning of September from Chicago. Taking a week off of work (plus the weekends) Any suggestions on where to head out to?

Head to Ohare and grab a direct flight anywhere. There are no good places within driving distance of Chicago.....Lake Geneva WI, New Buffalo MI, Door County WI, amish country. Yawn. Not to great of options unfortunately.

Now, let's not be so negative. It's true the pickins'are slim for weekend trips, but you CAN take road trips from Chicago, you just have to get through the dull stuff for a few hours.

My suggestions would be drive around the Michigan mitten; head to the Blue Ridge mountains of North Carolina; or go up 90 to 61 north and take that spectacular drive along the Mississippi.

There's a travel writer in the Tribune, Alan Soloman, who does driving trip stories, some of which you could maybe find on the paper's website. He had a great one about driving the Michigan mitten, for example.

This trip is for a whole week. Anywhere besides the boring neighboring states?(already done that).

Don't know your ages, if kids will be going along or interests, but. Have you been to the Black Hills of South Dakota -- Custer State Park, Rapid City, Mt. Rushmore, Deadwood, Gambling, Wind Caves etc. It is about 12 hours to Sioux Falls and then another six to the Hills. Should be quite doable for the week.

Other suggestions are Nashville or Gatlinburg, Tennessee.

Go to Canada!

Go on a road trip that I've always wanted to go on & report back...LOL!
I live in the Chicago area & think a trip to New Orleans, w/ a stop in Memphis to see Graceland would be a good weeks trip.

We've taken road trips from Chicago to the following:

Memphis, over to Hot Springs, up through Branson (Susan's suggestion for New Orleans is better)

Cedar Point in Sandusky Ohio to Niagara Falls to Toronto and back

To Atlantic City NJ, via several civil war sites, Pittsburgh, Hershey, PA, Baltimore, Philadelphia

Smoky Mountains