Filtered to Chicago. Switch origins below. Showing train and drive trips only.
3 picks from Chicago.
Sand, oysters, the kind of porch where the day just goes.
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.
Trees, trails, fires, fewer people. The cabin kind of weekend.
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.
Drafted by our agent, kept on the list when they hold up. Labeled honestly.
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.
