You may want to consider New Buffalo, MI area.

You can rent a car as it's a short drive but you may want to take Amtrak train instead.

http://www.harborcountry.org/

There are 7 Hiawatha Service trains per day from Chicago to Milwaukee. Fare for 2 is $46 or less with a discount. AAA?

watch this video

http://www.harborcountry.org/videos/

and look at the pics

http://www.harborcountry.org/through_your_lens/

and it's less than 2 hours away from beautiful downtown Chicago

Thanks, i'll check those links out. Milwaukee is definitely not going to be a possibility, hubby is spending the previous week there for busineess, so looking for elsewhere to visit and explore...

You might want to check out Door County in Wisconsin. I think it is about a 5-6 hour drive depending on whether you poke along the lakefront or take the highway. Great place for walks, scenery, and fish. It sort of reminds us of the Bar Harbor area in Maine without the salt water smell.

I've never been there but my chicago sister in law loves going to Galena once in a while. It look s nice and has rolling hills so the scenery must be pretty. You might want to google "covered bridges " in case there are some on a side route on the way. Here is one website I found:

http://www.coveredbridgemap.com/il/

http://www.visitgalena.org/index.cfm

When we lived in Chicago we used to take short trips to Door County,WI, American Club in Kohler,WI and New Buffalo, MI. We alos went to Galena once but moved on after a few hlurs.

Drive around Lake Michigan to Saugatuck and Douglas. Great little downtown areas. Or Detroit is only 5 hours from Chicago. We have The Henry Ford which has an indoor museum and an outdoor village. The Detroit Institute of Arts, the Rouge Plant has tours. Great dining options.

We recently visited Ann Arbor. It is a lovely town and not too far from Detroit.

Starved Rock State Park is very popular and not far. You can rent bikes downtown and ride 7 miles north or 10 miles south on the lakefront.

http://chicagovisitor.net/