The trip from the Chicago NW Suburbs to Monroe, Wi is 90 minutes to 2h depending on the route, which is great for an unplanned Friday evening getaway. You can take the tollway or IL 20 from the start, but unless you enjoy Rockford traffic, you will probably be on Interstate 90 and 39 south for couple miles until you take off west on IL 20 to Freeport. Then take IL 26 which becomes WI 69 when you cross the state line. Monroe is just a few miles north.
Map of Monroe WisconsonThe Gasthaus model is on the south side of the city, on the left side of the road. There are only 11 rooms, so you might want to make a reservation. http://www.gasthausmotel.com or 608-328-8395. If you arrive early enough, your hosts can hook you up with a great fish fry.
Gasthaus: On WI 69 in Monroe, WI
There are a number of good places for breakfast in town. We have tried both the Blue Ox and the Little Red Apple.

If you like looking out over rolling hills, farmland and streams, the views from WI 69 going from Monroe to New Glarus are some of the best in the state. It is incredible.

Once you get to New Glarus, there is the New Glarus Bakery, which has been serving great stuff for almost 100 years. But down on the more level side town, there is a great place for coffee served steaming hot in white porcelain mugs, not paper. The Fat Cat Coffee shop is at 606 Railroad St., which is to the left after you turn from WI 69 to 6th Ave. (WI 39.) They also have homemade pastry and sandwiches. There is often music on the patio out back.

One of the great things about New Glarus is taking WI 39 out of town to the west. 39 is the mountain ridge road. There is a Rustic Road about 2 miles west, and as you go farther, you have many choices. You can take WI 78 south and cut through the rural roads to the southwest and head to Poopies in Savanna, IL or Galena. You'll enjoy 39 until you reach Mineral Point and then catch 151 down to the Mississippi River. Taking WI 78 north leads you to Mt. Horeb. It is hard to go wrong with all the choices.