Chicago or Virginia Beach?

Virginia Beach is built around its beach, and that is where the gap lies. A wide strip of ocean sand runs about 5km along the boardwalk, with surf near the fishing pier, calm bay water at First Landing for small children and a quieter line of dunes at Sandbridge.

Chicago's beaches on Lake Michigan are a pleasant surprise, from Oak Street beneath the Gold Coast towers to the volleyball crowd at North Avenue. The fresh water is cooler, though, and a change of wind can chill it overnight, so a swim there fits between sights rather than filling the day.

Chicago is far ahead here. It has its own street classics, such as deep-dish and tavern-cut pizza, Italian beef and the hot dog without ketchup, along with the West Loop's restaurant row and serious Mexican, South Asian, Vietnamese and Polish cooking spread across its neighbourhoods.

Virginia Beach does one thing well: Lynnhaven oysters and Chesapeake blue crab, best eaten dockside near the inlet. Along the resort strip you mostly get chains and seafood buffets, and anyone wanting more variety drives to Norfolk.

Chicago is one of the world's great places to see architecture. You can follow the skyscraper from early steel frames and the Rookery to Mies van der Rohe, take the river cruise, see Wright's houses in Oak Park and finish at the Art Institute's Impressionists.

Virginia Beach has a few sights tied to the first English landing in 1607 at Cape Henry, an old lighthouse and an early colonial brick house. For anything more substantial you have to leave the city.

Chicago nights go on long after Virginia Beach has gone to bed. Bars stay open into the small hours, and each neighbourhood has its own scene: cocktail bars in Logan Square, clubs in River North, Northalsted's gay district, and dance nights rooted in the city's house music.

Virginia Beach's evenings are summer evenings on Atlantic Avenue, with beach bars, rooftop decks and a cheerful mix of vacationers and sailors. Out of season the strip goes quiet early.

Virginia Beach has more wild ground on its doorstep. There are the cypress swamp and maritime forest of First Landing, the empty barrier shore of Back Bay and False Cape, and kayak trips out to dolphins feeding offshore.

Chicago's outdoors is mostly the lakefront path, a long, flat run past harbours and the skyline that is very good for cycling. For dunes or canyons you have to travel to Indiana Dunes or Starved Rock.

Virginia Beach has the stronger day out. Williamsburg, Jamestown and Yorktown, about an hour's drive away, cover the American story from the first settlement to the end of the Revolution. Norfolk's battleship and Kitty Hawk on the Outer Banks are also within reach.

From Chicago, Milwaukee is an easy train ride and Oak Park is close by, but the open prairie gives little else that is worth the trip.

Both cities work well with children, but they offer different kinds of trip. Chicago is a museum vacation: the coal mine and U-boat at the Museum of Science and Industry, dinosaurs and belugas on the Museum Campus, and a free lakeside zoo.

Virginia Beach is a sandcastle vacation, with gentle bay beaches for toddlers, the aquarium's sea turtles and otters, mini-golf, and costumed tradespeople at Colonial Williamsburg nearby. Hotels and rental houses there are set up for families.

In Chicago you can get around without a car. The L runs from both airports into the Loop, and the main sights are a walk apart on a flat grid. Crossing between neighbourhoods is slower, and January wind makes walking hard work.

Virginia Beach is walkable only along the boardwalk and the trolley route. Sandbridge, First Landing, Town Center and every day trip mean driving through suburban sprawl.

Chicago gives shoppers a proper city to work through: flagships on the Magnificent Mile, luxury labels on Oak Street, the Tiffany ceiling of the old Marshall Field's, and independent shops in Wicker Park and Andersonville.

In Virginia Beach, shopping means a regional mall, chain stores at Town Center, and surf shops and souvenir stands at the Oceanfront.

Virginia Beach is the slightly gentler bill, especially out of season, when rooms that are expensive in summer drop sharply. The beach, the boardwalk and the state parks cost next to nothing, but a hire car eats into the savings.

Chicago's downtown hotels and their heavy taxes are the main expense. Cheap taquerias, the L and free sights such as Millennium Park and the lakefront help balance that.

This is one of the widest gaps between the two cities. Chicago has a world-class orchestra at Symphony Center, a full opera season, Steppenwolf and dozens of storefront theatres, nightly improv at Second City, and electric blues and late jazz sets in its clubs.

Virginia Beach offers a summer amphitheatre for touring rock and country acts and free stages along the boardwalk. Opera, the symphony and the spring arts festival are all in Norfolk.

Chicago is the one with somewhere to sweat. A Wicker Park bathhouse has kept its Russian and Turkish steam rooms and icy plunge pools going since the early 20th century, and a Korean bathing hall north of the city has heated rooms and pools for a long, lazy afternoon. When the city is under snow, the Garfield Park and Lincoln Park conservatories offer tropical warmth under glass.

Virginia Beach has nothing like that apart from hotel spas, so rest there depends on when you go rather than where you book a treatment. A dawn stroll along the sand before the resort wakes, or a stay in spring or autumn when the Oceanfront empties, feels slower than anything Chicago's streets offer. In high summer, though, the strip is as crowded and noisy as any city.