Chicago or Williamsburg, Virginia?

Chicago has the better beach life simply because the beaches are part of the city. Oak Street Beach sits right below the Gold Coast towers, and North Avenue's volleyball strand is a short walk from downtown. The freshwater lake is cool, though, and the swimming season is short.

Williamsburg is inland, so every beach day is a drive: the small strip at Yorktown, the bay at Buckroe or the Atlantic at Virginia Beach, an hour away. That water is warmer and the season longer, but sea nettles drift in during high summer, and most visitors swim in the hotel pool.

Chicago is one of the great American eating cities, and Williamsburg is a small town that feeds tourists. In Chicago a trip can run from Italian beef and tavern-cut pizza to tasting menus on Randolph Street, with whole neighbourhoods given to Mexican, Vietnamese or Polish cooking.

In Williamsburg the high points are simple: a country ham biscuit, Chesapeake oysters or soft-shell crab in season, and wine from the nearby vineyards. The candlelit colonial taverns are about atmosphere, and Richmond Road is mostly chains and buffets.

Chicago offers more breadth. It is a world-class architecture city, from the Rookery and the early Loop towers to Mies van der Rohe and Wright's Robie House, and the Art Institute and the Museum Campus can fill several days.

Williamsburg goes deep on one subject Chicago cannot touch, the eighteenth century. Its streets are a careful re-creation where costumed interpreters work the forges and print shops, and the Wren Building is the oldest college building in the country. It is absorbing, but two or three days covers it.

Chicago goes out properly, neighbourhood by neighbourhood: cocktail and dive bars in Wicker Park and Logan Square, dance clubs in River North with the city's house-music roots behind them, and Northalsted for gay nightlife. Bars pour until 4am.

Williamsburg barely has a night scene. There are student pubs near William & Mary and a few taprooms, and a ghost walk is usually the late finish. Anyone wanting more drives to Norfolk or Richmond.

Chicago edges ahead, mostly because its best outdoor day starts at the hotel door. The lakefront path runs about 29km past harbours and parks for walking or cycling, and there is birding in Jackson Park and kayaking among the towers. Indiana Dunes is about an hour away.

Williamsburg's Tidewater is softer and greener, with tidal creeks, ospreys and eagles from a kayak on the Chickahominy, and the quiet Colonial Parkway for a ride. Both places are flat, but here you need a car and should expect mosquitoes and humid summers.

Williamsburg is the stronger base for outings. Jamestown and Yorktown, two pillars of early American history, are each under half an hour away. The James River plantation houses line Route 5, and Richmond is about an hour off. You will need a car for almost all of them.

From Chicago, the prairie makes most outings an effort. The train to Milwaukee and a walk among the Wright houses in Oak Park are the easy wins. Lake Geneva and the Michigan harbour towns are pleasant drives rather than strong reasons to go.

Both are excellent with children, but in different ways. Chicago is a museum city for kids, with the coal mine and U-boat at the Museum of Science and Industry, dinosaurs, belugas and a planetarium side by side, and a free zoo by the lake. Plan around the bitter winters.

Williamsburg mixes thrill rides at Busch Gardens and Water Country USA with hands-on history, from musket firings to climbing aboard the replica ships at Jamestown. Motels with pools make it easy, though summers are steamy and every move means the car.

Chicago is far easier without a car. The L runs from both airports into the Loop, and the main sights sit within walking distance of one another on a flat grid. The weak spots are crossing between neighbourhoods by bus and walking in January.

In Williamsburg, only the Historic Area, Merchants Square and the campus are walkable, about 20 minutes end to end. Everything else, including the parks, the outlets, Jamestown and Yorktown, is spread along highways, and the buses are too thin to rely on.

Chicago is much the stronger shopping city, because it covers every level in one place. American flagships and department stores, luxury labels and independent boutiques all sit within a short ride of one another, so a serious shopper can fill a day. Its weak point is local character, since there are few markets or crafts and most of what you find is American brands.

Williamsburg reverses that balance. The choice is thin, with outlet chains on the highway and almost nothing in the way of fashion. Its colonial workshops, though, sell things Chicago does not: pewter, pottery and books made the eighteenth-century way. Here shopping is part of the history visit, not a reason to come.

Williamsburg is somewhat kinder to the wallet, mainly because rooms are plentiful and reasonably priced outside peak weeks. The catch is that a rental car is near unavoidable, and each of the big attractions charges a hefty admission.

Chicago's downtown hotels, sit-down restaurants and taxes push costs up, especially in summer. The free things are real, though: the lakefront, Millennium Park, Lincoln Park Zoo and cheap taquerias, plus an L that saves you a car.

This is one of Chicago's strongest suits. It has the Chicago Symphony Orchestra, a full Lyric Opera season, Steppenwolf and the Goodman, improv at Second City every night, and electric blues in club rooms across the North and South Sides.

Williamsburg's performances belong to its setting: candlelit recitals of period music, fife-and-drum corps on Duke of Gloucester Street, and student concerts in term. For a professional orchestra or theatre, you drive to Richmond or Norfolk.

Neither is a place people come to unwind, and they offer much the same amount of calm. Chicago's version is livelier: an old Russian-and-Turkish bathhouse in Wicker Park with steam rooms and cold plunges, plus warm conservatory glasshouses in winter.

Williamsburg has no bathing culture, only resort and inn spas. Its slower overall pace does the rest: empty colonial greens early in the morning and unhurried drives along the wooded Colonial Parkway.