90 minutes by car or trainAmtrak Hiawatha from Union Station, 90 minutes
Famous for: Friday fish-fry tradition, Old Fashioned cocktails, beer halls
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.
3 hours by carDrive west on I-90, exit at Galena
Famous for: Wineries, riverwalk dining, inn breakfasts
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.
75 minutes by carDrive east on I-90 then I-94 to exit 1
Famous for: Lakefront dining, Round Barn Winery, summer kitchens
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.
90 minutes by carDrive northwest on I-90 to Lake Geneva exit
Famous for: Lakefront patios, Italian on the lake, ice-cream parlours
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.
40 minutes by carDrive south on I-94 to Indiana 312 exit
Famous for: South Asian markets, Indian and Pakistani restaurants
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.
60 minutes by carDrive east on I-90 to Chesterton, Indiana
Famous for: Beach-edge fish shacks, smelt fry, dune hikes
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.