Minneapolis to Chicago drive: 24 ranked stops, break in Black River Falls

Logan Square neighborhood pioneer since 1999 serving seasonal market-to-table cooking that earned a James Beard hospitality award. Order: Farmer's breakfast.

This park centers on Pierce and Olson lakes, with hiking, mountain-bike, and equestrian trails plus fishing and boating. One trail segment south of the concession is closed for reconstruction through early 2027, so check the IDNR closure page.

Mirror Lake sits below pine-and-oak woods and sandstone cliffs reaching about 50 feet. Hiking remains possible in 2026, but roadwork closes the boat launch, several facilities, and trail access points, so travelers should check current conditions before detouring.

Romantic French-Vietnamese restaurant with an open interior and patio, known for house pho and locally sourced ingredients. Order: Grande Soupe pho.

More than five miles of trails cross white-oak woods, prairie, fen, and lakeshore. A short wetland boardwalk ends at a wildlife-viewing platform, while the crushed-limestone Prairie Trail provides a gentler accessible option.

Karyn Tomlinson's Best Chef Midwest winner in St. Paul, a grandma-chic tasting menu celebrating Minnesota farmers with precision. Order: Tasting menu.

a city-park fall made famous by Longfellow’s poem

Thirteen miles of trails cross prairie, forest, and the Willow River valley, with Willow Falls and nearby overlooks as the main destination. The 0.4-mile falls route is short but steep; longer river-bottom routes provide a more gradual outing.

All-Wisconsin tavern named for the state cocktail, steps from the Capitol and the Dane County Farmers' Market. Order: Beer-battered cheese curds.

a fun, flowy network near Madison

A nearly 50-year Pilsen family institution reopened in 2026.

a wide multi-tier fall in Willow River State Park near the Twin Cities

The Dakota call this spot Bdote -- 'where two waters come together' -- and it's literal: walk the Pike Island trail and watch the muddy Minnesota River visibly merge into the clearer Mississippi, one of the few confluences in America where you can see two rivers' colors mix in real time from dry land.

Ann Kim's south Minneapolis neighborhood pizzeria turning out lightly charred wood-fired pies including the Korean barbecue and My Sha-Roni. Order: Korean BBQ pizza.

a clifftop over the Wisconsin River

a hidden slot gorge and falls near Baraboo

a steep climb past a famous balanced quartzite boulder

a German-style brewery with a popular Bier Garten near Madison

Trails cross the remains of a fortified Middle-Mississippian town occupied roughly A.D. 1000-1300, including reconstructed stockade sections and two restored platform mounds. The open prairie setting makes the village plan easier to read than at a conventional artifact museum.