Metro Chicago and Southern Wisconsin Vacation Ideas Metro Chicago and Southern Wisconsin - Road Trip Planner

Chicago Scenic Drives - Illinois, Milwaukee, Wisconsin Dells, Madison

Things to do / Travel Guide

With prairie lands galore in southern Wisconsin, and with Chicago's recognizable and awesome architecture and skyline, there's almost always something to see in this region. From Lake Michigan to Lake Geneva, beautiful drives are all around you.

Chicago-area Scenic Drives

The 18-mile drive along Lake Shore Drive is stunning! Hug the curves of Lake Michigan with the glistening waters to your east and to your west Lincoln Park, the Hancock Tower shimmering in the sun, and the Navy Pier Ferris Wheel peering out at you. Start on North Lake Shore Drive on the northern edge of Chicago as it changes names from Sheridan Road, and get a taste of the water as the wind runs through your hair through near-constant parks. In Grant Park you'll have the chance to view Buckingham Fountain and Museum Campus; then its views of the skyline, and parks alongside the road, all the way down to Jackson Park.

Southern Wisconsin Scenic Drives

If you're searching for a historic scenic route, or a good area to drive around more or less aimlessly, look no further than in Racine, Wisconsin. Three Mile Road, beginning at 108th Street, and heading east to 80th Street, was originally laid out in the early part of the 19th century, and looks virtually untouched. Old oak and rail fences still line the area, plus there are tons of rustic roads to peruse around, like Honey Lake Road, and Maple Lane. There are plenty of views of woodland preserves, dairy farms, and even muskrat homes.

In Milwaukee, North Lincoln Memorial Drive, which parallels State Road 32 and from which it branches off at E. Kenwood Boulevard, provides more great Lake Michigan views. You can start at Lake Park and finish at Veteran's Park. While driving on this coastal highway you'll pass Villa Terrace, which houses beautiful decorative arts and is gorgeous from the outside, and the Milwaukee Art Museum with its magnificent winged design. This drive is all of 10 miles long.

John Nolen Drive, Madison, WI

Along Lake Monona in Madison, on the isthmus between this lake and Lake Mendota, you'll find the scenic John Nolen Drive. A quick ride of about three miles southeast on this road, and you'll pass sites like the Frank Lloyd Wright-designed Monona Terrace Convention Center and the State Capitol. Once at the other side of John Nolen Drive, the lake's southernmost tip, there are splendid views of Olin-Turville Park. This drive can clear anyone's head and put them in a good mood, with the beautiful foliage and frequent sightings of deer.