Chicago or Louisville?

Of the two, only Chicago has a beach life. More than twenty sandy beaches line Lake Michigan within the city, from Oak Street right beside the Gold Coast towers to the volleyball crowd at North Avenue. In high summer the fresh water is warm enough for a real swim, and lifeguards are on duty.

Louisville has no equivalent. The Ohio is a working river with barges and strong currents, so swimming means a pool or a drive out to the reservoir lakes in the countryside. Chicago's swimming season is short, though, so even there the lake is an extra on a summer afternoon, not the reason for the trip.

Chicago has the bigger and more varied food scene. It has its own street food, including deep-dish and tavern-cut pizza, Italian beef and the dressed hot dog. The tasting-menu kitchens on Randolph Street sit above that. In the neighbourhoods you find Mexican cooking in Pilsen, South Asian on Devon Avenue and Vietnamese on Argyle Street.

Louisville's food is narrower but has a strong identity. Bourbon comes first, with the bars on Whiskey Row and distillery tasting rooms downtown. After that come the hot brown, burgoo and Derby pie, served in restaurants in NuLu, the Highlands and Butchertown. Go to Louisville for whiskey and Southern cooking. If you want many different cuisines in one trip, Chicago is the better choice.

Chicago is where the skyscraper developed after the 1871 fire. A walk through the Loop or a river cruise shows that history, from the Rookery's light court to the glass towers by Mies van der Rohe. The Art Institute and the three museums on the lakefront Museum Campus add enough to fill a week.

Louisville's sights are smaller and follow a few themes: Churchill Downs and the Derby Museum, the Muhammad Ali Center, and the Louisville Slugger Museum among the cast-iron fronts of Whiskey Row. The Victorian mansions of Old Louisville make a pleasant afternoon walk. Altogether the city holds about two or three days of sightseeing.

Both cities have bars that stay open very late, but Chicago's nightlife is far bigger. Each neighbourhood has its own scene: cocktail and dive bars in Wicker Park and Logan Square, dance clubs in River North, and the gay district in Northalsted. Its clubs also carry on the house music the city helped create.

In Louisville a night out means bars rather than clubs. Most people go to the patios and dive bars along Bardstown Road or the bourbon bars in NuLu, while groups head to Fourth Street Live. The city is at its liveliest around the Derby in spring.

Both cities offer pleasant green space rather than dramatic scenery, but the landscapes differ. Chicago is flat and centred on the lake. Its long shoreline path is best done by bike, and it also has birding along a migration route and kayaking among the towers on the river.

Louisville has more varied ground. Olmsted's Cherokee and Iroquois parks have wooded hills, the Falls of the Ohio have fossil beds you can walk out on, and Bernheim Forest and Mammoth Cave are within a short drive. Choose Chicago for water and skyline, or Louisville for woods and hills.

Louisville has the better day trips. Bardstown and the distillery country are less than an hour away, and the thoroughbred farms and Keeneland racecourse near Lexington are only a little further. Shaker Village and Lincoln's birthplace are also easy outings, though nearly all of them need a car.

From Chicago the choice is thinner. Milwaukee is easy by train and Oak Park is on the edge of the city. Beyond those, the options are lakeside drives into Wisconsin or southwest Michigan, which are pleasant but rarely the high point of a trip.

Chicago has more to fill a family stay. The Museum of Science and Industry, with its coal mine and U-boat, can take a whole day, and the Museum Campus puts dinosaurs, beluga whales and a planetarium side by side. Lincoln Park Zoo is free, and the lake beaches have lifeguards in summer.

Louisville is easier going, with a zoo, a hands-on science centre and Kentucky Kingdom's coasters and water park. Its most unusual outing is the Mega Cavern, an old limestone quarry under the city with ziplines. The attractions are spread out, so families need a car, while in Chicago the hardest part is the winter cold.

In Chicago you can manage without a car. The L takes you from either airport to the Loop, and the flat, gridded centre is easy to walk. The main drawback is that the lines run in and out of downtown, so getting from one neighbourhood to another often means a long bus ride.

Louisville has no rail transit at all. Downtown and NuLu are walkable, but Churchill Downs, the Highlands and the big parks all need a car or ride-hailing. The traffic is light, though, so driving is easy.

Chicago is a real place to shop. The Magnificent Mile and Oak Street have flagship stores and luxury labels. The old Marshall Field's building on State Street is worth seeing just for its Tiffany mosaic ceiling. Wicker Park and Andersonville have independent boutiques.

Louisville's shopping is small and local: design shops in NuLu and vintage clothes, records and antiques along Bardstown Road. The best thing to bring home is local, a bottle of bourbon you rarely find elsewhere, or a Derby hat.

Both cities cost roughly the same overall, but the money goes in different places. In Chicago, the biggest costs are downtown hotels and the taxes added to them. Daily life can be cheap, with taquerias, hot dog stands, the L and a free lakefront and zoo.

Louisville is the other way round. Hotels are reasonable outside the racing season, but meals, tips and a hire car add up every day. During Derby week, room rates jump several times over, so budget travellers should avoid it.

In Chicago, live performance can be the main reason to go. It has a world-class symphony, the Lyric Opera's full season, Steppenwolf, the Goodman and many storefront companies, plus nightly improv at Second City. Electric blues and late jazz sets play across the city.

Louisville has a full set of companies for a city its size. The orchestra, opera and ballet perform at the Kentucky Center, and Actors Theatre has long staged new American plays. Bluegrass and Americana bands play in the bars on Bardstown Road. It is a solid programme for an evening or two, but Chicago offers far more.

Neither city is a place for a relaxing retreat, but Chicago has more to offer. A Wicker Park bathhouse that has run since the early 1900s still has scorching steam rooms and cold plunges, and there is a Korean-style jjimjilbang in the suburbs. The warm glasshouses at Lincoln Park and Garfield Park are good escapes in winter.

Louisville has only hotel and day spas. What it has instead is a slower pace, with afternoons on a porch in the Highlands or a drive through horse country. For a real spa stay, the old mineral-spring resorts at French Lick and West Baden Springs are about an hour and a half away by car.