The list keeps growing. The picks stay opinionated.
7 picks from Chicago.
A college town that grew up without losing the farmer's market. Two and a half hours from Chicago gets you Saturday morning on the Capitol Square with cheese curds that cost $4 and taste like the reason Wisconsin matters. Stay on the isthmus, walk the lakes, eat dinner at a restaurant that would work in any city but costs what it should here.
A Lake Michigan beach town 90 minutes from Chicago, where the sand is actual sand and the wine bars close at 9pm. Two nights gets you a Saturday on the beach, a Friday-night dinner that earns the drive, and a Sunday morning at the farmers market before the route back is all brake lights.
Four days in a city that eats dinner at 10pm and means it. Palermo Soho for coffee and leather goods, San Telmo for the Sunday market that locals actually attend, and a parrilla where the waiter brings you exactly what you need without asking. BA is the European-feeling city that costs half what Europe does.
A Victorian island in Lake Huron where cars have been banned since 1898. You arrive by ferry, check into the Grand Hotel with its 660-foot porch, and spend two days moving at the speed of a horse-drawn taxi. Fudge shops are unavoidable but the island is bigger than its kitsch.
A Mississippi River town that peaked in 1850 and knows it. Main Street still runs on brick and iron storefronts, the best hotel is an 1855 mansion on a hill, and the whole town shuts down by 9pm in a way that feels like the point. Go in October or March when the tour buses stay home.
Four hours north of Chicago, Door County stops being a summer destination in late September and becomes something better. Orchards you can walk through, fish boils that aren't performance art, a peninsula that empties out the week after Labor Day.
A Michigan harbor town that figured out how to be a beach destination without losing its mind. Galleries on Water Street, a dune climb that earns the lake view, and a hotel that used to be a chain saw factory. Two hours from Chicago and it feels like you crossed a border.
