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