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Anywhere from Chicago
From O’Hare and Midway, a surprising number of beach and mountain trips are a single flight, and several good weekends are a drive.
These are places with enough of a reason to leave O'Hare, not a thin list of every airport code we know. Prices are not shown here because a fare without a live source would be a guess.
Orlando
Theme parks, warm water, and a flight that is nonstop from a lot of US cities.
Late January through early May, and again in November, when the parks are cooler and slightly quieter.
Cancún
A beach reset with meals included, close enough for a long weekend from much of the East and Midwest.
December through April for drier days. Summer is hotter, cheaper, and still very swimmable.
Nashville
A city trip with a short flight from much of the country.
April, May, October, and November. Summer is hot and the honky-tonks do not get quieter.
New Orleans
A city with a point of view, reachable from most of the South in a short hop or a drive.
February through May, and late fall. Summer is a steam bath with excellent food.
Denver and the Rockies
Mountains without committing to a resort town price on night one.
June through September for high trails. December through March if the wish is actually about snow.
Asheville
Mountains and a walkable downtown, often as a drive.
April through June and September through November. Leaf season books up.