bria_68, I'm confused and maybe you can clarify for me...

Some of the places you mentioned above are much further than 2-2.5 hours' drive from Chicago. Galena, for example, is more like 4-4.5 hours and Brown County is at least 3.75-4 hours.

Are you saying that something within that type of driving time is OK as well?

And...are you only speaking of driving - or flights as well?

Hi exiledprincess. Thank you for responding. We will be driving but don't want to drive more than 2.5 hours. I mentioned some of those places just in case someone suggested them since they are not much farther. I hope this additional info helps. Thank you!

Have you been to Kohler, WI? The American Club has spa facilities, golf, plenty of good restaurants and specialty shops. The Inn At Woodlake is another hotel on their property and I think it is a bit less expensive. We always enjoy looking around at the Kohler Design Center. They have wonderful kitchen and bath displays set up. I've included the link.
http://www.americanclubresort.com/index.html

Depending on how long you will be staying you might want to check out the city of Sheboygan. It is nearby on Lake Michigan with some nice beaches and shops set up along the river walk. The John Michael Kohler Art Center is there if you enjoy that sort of thing. You need to check out the bathrooms. Strange as that sounds you may have seen them featured on national TV because of the interesting tile work. Don't forget to crash the men's room. The Blue Harbor Resort is right on the lakefront. I haven't stayed there but it is a nice place to have a drink on their patio overlooking the water.

Hello mdwest. I have not been to either Kohler nor Sheboygan. I will definitely look up info on these. Thank you for your suggestions! Take care.

You are very welcome.
If you do head to Kohler, you and your friends might enjoy a stop in Cedarburg on your way north. It is a quaint town just north of Milwaukee with lots of nice shops, galleries and antiques stores. We always enjoy stopping in at Cedar Creek Settlement. It is a converted mill filled with interesting shops and lots of winding staircases, nooks and crannies. I used to miss some of the shops because I didn't find the right staircase.
http://www.cedarburg.org/Attractions-Fall.htm

Whatever you choose, have a good time.

Indianapolis. It's the 12th largest metropolitan area in the U.S. If you cannot find something really interesting to do there, I'd be very surprised. www.visitindy.com

You might particularly enjoy Broad Ripple(discoverbroadripplevillage.com) or Carmel (www.visithamiltoncounty.com).

But not too far away, or on the way there, there are a couple of options as well:

In West Lafayette (about 1 hour north of Indianapolis), at historic Fort Ouiatenon, the Feast of the Hunter's Moon: www.tcha.mus.in.us/feast.htm This is a really nice festival to experience, especially when you have the delightful autumn weather. If you do decide to go, make sure you are there in the morning when they have the dress parade (if you look at the schedule, you can see all of the corps who attend in period dress) and fire the cannon at the fort. The canoe races are very fun and exciting to watch, as are the Native American dances. I've gone several years and always learn something new about that long-ago period.

If you like architecture, then Columbus, Indiana is the place for you: www.columbus.in.us

On the way back from Indy, you could always take U.S. #41 north, instead of I-65. What a wonderful, windy drive through the beautiful fall folliage! Parke County has the largest concentration of covered bridges in the U.S.

I used to go to the Covered Bridge Festival in Rockville for many years, before it got sooo congested; however, if you go at a different time than the festival, you can still see them without the crowds. Antique and junk shops with "collectibles" along the way. You can pick up maps of the bridge locations in Rockville and seek them out yourselves. http://coveredbridges.com

Of course, you could go to French Lick and/or West Baden, Indiana: www.frenchlick.com