Toronto
Long mocked by Montrealers as a soulless banking town and despised by the rest of Canada as, well, a soulless banking town, in reality Toronto has been the entertainment capital of Canada for years and has even eclipsed New York and London in terms of sheer variety of divertissements. Toronto's big-budget productions are often just imports from those theatrical powerhouses, but luckily the city boasts more than 200 smaller theatre companies, the summer Fringe theatre festival and the annual Dream in High Park Shakespeare performance. The new Four Seasons Centre for the Performing Arts has finally given the Canadian Opera Company and the National Ballet of Canada the performance venue they deserve. Music acts play spots as diverse as the Molson Amphitheatre, Roy Thomson Hall, Lee's Palace, the Horseshoe Tavern and the sublime, 113-year-old Massey Hall. The annual Caribana festival turns the city into party central. How about countless state-of-the-art cinemas in a fervent movie town that hosts what is arguably the best film festival in the world for fans? Maybe a baseball, basketball, hockey or even soccer game is more your style. And to round out the night, dance into the wee hours in the city's raucous, even out-of-control club district. Who's laughing now, Montreal?
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Las Vegas
Say what you will about America's id, but at least this city knows what it is and what it does best. Sure, Las Vegas went astray a few years ago and flirted with the idea of becoming a family destination, but a few stiff drinks later it was back on track as an adult-rated fun zone. Gambling may not be your bag, but where else can you find such a wonderfully absurd array of shows? Five different Cirque du Soleil spectacles, magic acts, top comedians and a long tradition of musical stars - a line of succession that extends from the city's Sinatra-led golden age through the Elvis years and into the current reign of Celine - mean there's always some over-the-top show in this over-the-top town. And the beauty of Vegas is that it has a stunner of an encore: After a night on the town, after Celine has belted out her last song for "the children," after you've lost your last roll of quarters, head out to the desert to watch the sun come up over nearby Red Rock Canyon. That's a show you won't want to miss.
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Chicago
Yes, Chicago. Perennially overshadowed by that big town to the east, Chicago - home to the always compelling Steppenwolf theatre ensemble - has a theatre and dance scene that is really second to none. Music? The city long ago inherited its wealth of jazz and blues musicians from the American South, and the city's bars and clubs are always packed with local and visiting talent. And for sports fans, the Bears, the Cubs, the White Sox, the Bulls and the Blackhawks mean there's almost always a game in town or on the sports bar's big-screen TV - so good with a bucket of ribs or a deep-dish pizza. But what makes Chicago such an entertaining city - apart from Oprah, of course - are the countless music festivals and free events along its much-envied waterfront and in its parks.
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Massimo Commanducci is The Globe and Mail's deputy travel editor. As a Toronto resident, he is never bored.