Chicago

Dunes, Cowles Bog & Lake Michigan Swim

Indiana Dunes National Park sits 60 minutes from the Loop and packs more ecological diversity into 15 miles than almost anywhere in the Midwest — boreal forest, oak savannas, and the crowning 126-foot sand dune of Mount Baldy rising directly above Lake Michigan's blue water.

Lake Geneva: Shore Path, Vineyard Afternoon & Wood-Fired Evening

Lake Geneva, Wisconsin is 90 minutes from Chicago and has been the Midwest's answer to Newport since Chicago industrialists began building estate cottages on its shores in the 1870s. The 26-mile Geneva Lake Shore Path — said to have been continuously used since the Potawatomi people inhabited the region — connects the surviving Gilded Age estates and runs past the 1933 Riviera bathhouse and the mail-boat dock, where a postal carrier still leaps from a moving boat to deliver lakefront letters. Staller Estate Winery outside Delavan rounds out the afternoon with estate-grown wines and small-batch spirits before wood-fired dinner at Oakfire back in Lake Geneva.

Milwaukee: Pabst Mansion, Art Museum & Brady Street

Milwaukee is 90 minutes from Chicago and constitutes one of the most underestimated city day trips in the Midwest. The Pabst Mansion documents the Gilded Age brewing wealth that made Milwaukee one of America's richest cities per capita; the Art Museum's Calatrava wing is among the most photographed buildings in America; Brady Street's historic ethnic commercial district shows what a walkable neighborhood looks like when it survives intact.