New Buffalo in Michigan is the 75-minute Lake Michigan day trip from Chicago, with downtown dining at David's Deli, Round Barn Winery and beachfront kitchens.
Tip: Round Barn Winery is the daytime stop; downtown New Buffalo for dinner. The dunes at Warren Dunes State Park are the morning hike.
Lake Geneva in southern Wisconsin is the 90-minute summer-kitchen day trip from Chicago, with lakefront dining at Pier 290, grills at Popeye's and ice cream nearby.
Tip: Take the mailboat ride first (90 minutes), eat at Pier 290 with a lake view second. Avoid Saturday traffic and go on a Tuesday.
Munster in northwest Indiana is the 40-minute South Asian day trip from Chicago, with a cluster of Indian and Pakistani groceries and restaurants along Ridge Road.
Tip: Lunch at one of the Ridge Road Indian-Pakistani spots, then Schoop's Hamburgers for the trip home; the Patel Brothers market stop is the take-home haul.
Indiana Dunes National Park is the 60-minute day trip east of Chicago, with the Dunes State Park, a spring Smelt Fish Fry weekend and shoreline dining nearby.
Tip: Combine the dunes morning hike with a fish-shack lunch at Schoop's in Munster on the way back. Whole trip eight hours.
Milwaukee in Wisconsin is the 90-minute Hiawatha-train day trip from Chicago for the Friday fish fry, with Lakefront Brewery, the Public Market and Old German Hall.
Tip: Plan the trip for a Friday; Lakefront Brewery's fish fry is the canonical destination. Old Fashioneds at Bryant's are the after-meal walk.
Galena in northwest Illinois is the three-hour weekend trip from Chicago, with riverside dining at Fritz and Frites, the Galena Cellars winery and a row of inns.
Tip: Weekend trip is the better use; book the General Dodge House for Saturday night and Fritz and Frites for dinner.