Chicago or Rehoboth Beach?

Rehoboth Beach is built for the beach and Chicago simply has some. In Rehoboth the wide pale sand and moderate Atlantic surf sit at the end of every street. Long ocean swims are possible in July and August, and Cape Henlopen and Delaware Seashore State Park offer wilder sand away from the boardwalk crowds.

Chicago's lakefront beaches are a real pleasure in their own way: freshwater swimming at Oak Street with the Gold Coast towers behind you, or volleyball at North Avenue. The lake is cooler, a change in the wind can chill it overnight, and most visitors treat it as a break between sights rather than the point of the trip.

Chicago is one of the great American food cities. Its own staples include deep-dish and tavern-cut pizza, Italian beef and the dressed hot dog, and it has serious tasting-menu kitchens in the West Loop. The real breadth is in the neighbourhoods: Mexican food in Pilsen and Little Village, South Asian on Devon Avenue, Vietnamese on Argyle Street.

Rehoboth eats well for a beach town, helped by its Washington crowd. Steamed blue crabs, raw bars and boardwalk fries give it a shore character, and its craft beer is genuinely good. The range is narrow by comparison, though, and much of it shrinks once summer ends.

The gap here is very wide. Chicago is where the skyscraper came of age, and a river cruise past the Loop's towers, the Robie House in Hyde Park, the Art Institute and the Field Museum could fill a week on their own.

Rehoboth's culture fits in an afternoon: the Rehoboth Art League's garden galleries in Henlopen Acres, the old camp meeting cottages and a small museum house. Visitors with an interest in history tend to drive to Lewes or to the wartime towers at Cape Henlopen.

Chicago goes out late and in every style, from Wicker Park cocktail bars and River North dance clubs to Wrigleyville sports bars, with house music woven into the club scene. Many bars pour until 4am, all year round.

Rehoboth's evenings have a character of their own. As a long-established LGBTQ resort, it has piano lounges and drag nights around Baltimore Avenue, while the deck bars in neighbouring Dewey Beach draw a younger, louder crowd. There are few real clubs, nights end earlier, and out of season it goes quiet.

There is little to choose between them on the outdoors, but the settings differ. Chicago's nature is urban parkland: the 29km lakefront path for cycling and running, birding in Lincoln and Jackson Parks, kayaking among the towers, with Indiana Dunes and Starved Rock a drive away.

Rehoboth has the wilder coast on its doorstep: Cape Henlopen's high dunes, salt marsh and pine woods, bay paddling, dolphins offshore and the Assateague ponies within an hour. Both are flat, so expect gentle outings rather than hiking with views.

Rehoboth has a slight edge for outings, mainly because Lewes, Delaware's oldest town, is ten minutes away, and from there the ferry crosses to Cape May's Victorian streets. Ocean City, Berlin and Chincoteague round it out, all by car.

From Chicago the best trip is Milwaukee by train, with Oak Park's Wright houses on the city's edge. Lake Geneva and the Michigan harbour towns need a car and a longer drive across the prairie.

Both work well with children, but Chicago offers more variety. The Museum of Science and Industry, the Shedd's dolphins and belugas, the Field Museum's dinosaurs and a free lakeside zoo give it full days in any season, as long as you plan around the winter cold.

Rehoboth is the easier, simpler choice for a summer week: lifeguarded sand a few steps from the rental, Funland's gentle rides on the boardwalk, and calm bay water at Cape Henlopen for toddlers. Outside summer there is little for children to do.

You can manage Chicago without a car. The L runs from both airports into the Loop, and the main sights downtown are within walking distance of each other. Crossing between neighbourhoods often means a bus, though.

Rehoboth is easy once you are there, with a compact grid, bikes everywhere and a trail to Lewes. Getting there is harder: there is no train, the highway clogs on summer weekends, parking is scarce, and every day trip needs a car.

Chicago has the bigger stage. The Magnificent Mile's flagships, luxury labels on Oak Street and the Tiffany ceiling in the old Marshall Field's store on State Street are the main draws, with independent fashion and record shops in Wicker Park and Andersonville.

Rehoboth's draw is Delaware's lack of sales tax, which fills the outlet centres on the highway, while Rehoboth Avenue offers small boutiques, galleries and bookshops. The style is resort casual, and there is nothing in the way of luxury streets or department stores.

Neither is cheap, and the costs come from different places. In Chicago, downtown hotels, heavy taxes and sit-down meals add up, but taquerias, hot dog stands, the L and free attractions like the lakefront and Lincoln Park Zoo make savings easy, especially if you stay outside the Loop.

Rehoboth's prices follow the season more sharply. High-summer rentals and weekend rooms come at a premium, but spring and autumn bring real savings, and the beach and the tax-free shopping cost nothing extra.

This is one of Chicago's strongest suits. The Chicago Symphony Orchestra, the Lyric Opera, Steppenwolf and the Goodman, nightly improv at Second City and electric blues in the clubs give you something worth booking every evening.

Rehoboth offers free bandstand concerts on summer evenings, a small theatre company staging musicals and cabaret, and an autumn film festival. For bigger shows you need to drive further into Sussex County.

Neither city is really built for unwinding, and each offers a different kind of rest. Chicago's comes through heat. In Wicker Park there is a century-old bathhouse where the steam is fierce and the plunge pool icy, and out in the northern suburbs there is a Korean bathing hall. Both are more of an experience than a hotel spa. On a grey winter afternoon the glasshouses at Lincoln Park and Garfield Park are warm, green and quiet, but outside them you are back in a big city running at full speed.

Rehoboth has little to offer in treatments beyond a handful of spas and yoga classes, so its calm depends on when you go. Come in June or September, or on an autumn weekend, and the boardwalk is nearly empty, the lanes under the pines are good for slow cycling and evenings are quiet. If you come for rest in July or August, expect the opposite.