my sister-in-law has law has said galena is a nice town to visit.
www.galena.org

memphis, etc. would take up all your quality time on the road, it seems to me. too far for two nights.

Kohler American Club, Kenosha area wisconsin is nice, on the lake and in upscale area.

For history and architecture, south to springfield illinois.
frank lloyd wright has a fabulous house there to visit.

lincasanova had a good idea in Kohler; there is a less expensive hotel than the American Club right on the property...save your $$ to eat at the American Club!
Door County, Wisconsin is also a good option.

Cedarburg, WI is a great spot with a few inns/ B&B's. We stayed at the Cedarburg Inn once, in the late 90's. I think it's 2 -3 hours north of Chicago. You could MapQuest it to make sure.

Here's the place we stayed at in Cedarburg (I had the name wrong): http://www.washingtonhouseinn.com/

I've done this throughout the areas mentioned. What do you like? Do you want to be on water? How laid-back?

Lake Geneva in WI is great- LakeLawn Lodge, I believe. But it's a little old for you and a maybe a bit too groomed.

Do you want wilder- how about going down sanddunes in a jeep rental - 100 feet plus straight down. Do you like B&B's? Lake Michigan side of the State of MI, might be what you want.

For low-key I would do Michigan Harbor Country or North of that, especially if you wanted vineyards, wine tasting or great sunsets.

Galena is nice, but IMHO if you want to stay close and do IL, I would much prefer the Starved Rock area myself as they have resorts etc. now too and I like the nature there and IL River area better, NOT tourist arcades & fudge shops etc. Galena in July gets to resemble the Dells. Easy simple no traffic ride to Starved Rock area as well.

Do you know that it is VERY late to be planning a late July stay, and most of these places will be all booked and you might have to hope for cancellations?

Have you thought about Milwaukee? It's more than just beer and brats.

http://p104.ezboard.com/feuropetogofrm12.showMessage?topicID=332.topic

Thank you to everyone who has replied. Those are all great ideas! I am looking into a bunch of them. And I have admit, I Milwaukee never even crossed my mind! I know I have to pull this together fast because alot of places are booking up. So far I think my top 3 contenders are Door County (Sturgeon Bay, I am thinking), Starved Rock, and Milwaukee.

Under $200 a night should be easy unless you are limited to high line hotels/resorts.

I agree that Memphis is too distant.

Low Key: Green Lake,WI Dubuque,IA LaCrosse,WI Green Bay,WI Wausau or Stevens Point,WI

Medium Key: Door County,WI Galena,IL Madison,WI Indianapolis or St. Louis.

Resorts (might push the $200 limit): Olympia in Oconomowoc,WI Grand Geneva in Lake Geneva,WI Blue Harbor Resort in Sheboygan, WI

As you can tell, I am a WI oriented guy, not much knowledge of MI.

Just saw your reply...

Rather than Sturgeon Bay look into Egg Harbour or Fish Creek. IMHO Sturgeon Bay is nothing special.

I'd add Spring Green and Madison as possibilities. House on the Rock resort if you stay in Spring Green. You could see Romeo and Juliet at APT and Talesin. The Sheraton on John Nolen Drive in Madison consistently comes up for $50 per night or so through priceline. If you haven't been to Madison, there is a lot to do here.

For fun you might want to check out biddingfortravel.com and see where you can get a great deal on a 4* property. That will allow you to stay in style and spend your money on other things.

We like to stay on the quieter eastern side of Door County, like Bailey's Harbor (no relation), and then take trips from there. In July it's lovely when the cherries are ripening. Door Co. is the Maine of the Midwest, lighthouses and all.

You mention Starved Rock. I love the lodge in the park. But I seriously doubt you'd be able to get reservations for a weekend in July at this point.

Western Wisconsin coulee region would be GREAT!-in the fall but not July so I would avoid that area.
I would come up to Milwaukee and do the Downtown Riverwalk and lake front for sightseeing. I think Marquette park on the river walk has free movies on Fri. night and music on wed. but check.
Lodging check into the airport location hotels. From there it is a simple 20 min drive to Milwaukee downtown/lakefront.
And additional spot that is very nice is downtown/lakefront Racine/. 35 min or so from Airport hotels. One on the last remaining Kewpee restaurants is in Racine. http://www.kewpee.com/

Both would make a comfortable relaxed and nice weekend.

Having just gotten back from my first trip in years to Door County (see my restaurant recommendation for upscale in Fish Creek - the Whispering Swan) - I echo the recommendation of Egg Harbor or Fish Creek over Sturgeon Bay. Egg Harbor has two large-ish old-fashioned "resorts" ... the Shallows and Alpine Resort. Peninsula Playhouse in Fish Creek has a good schedule and lovely setting on the water (and uses lots of Chicago talent - artistic director is Greg Vinkler who's a regular at Chicago Shakespeare and Court Theater) There is music at Birch Creek and elsewhere, lots of nice walking and bicycling (rentals easy at Peninsula State Park if you are not bringing your own).