A perfect day in Chicago

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Writer Nelson Algren summed up Chicago best: ‘Like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.’ There’s something about this cloud-scraping city – its blend of high culture and earthy pleasures – that bewitches.

Morning art

Energize for the day ahead at Lou Mitchell’s (565 W Jackson Blvd, Loop) near Union Station. The old-school breakfast joint sprang up in Route 66's heyday, and waitresses still deliver thick-cut French toast and plate-defying omelettes – along with free doughnut holes and Milk Duds – near the fabled road’s starting point.

Use that sugar buzz to walk east a mile, under the clackety El train tracks, through downtown’s money-spinning core, to the Art Institute of Chicago (111 S Michigan Ave, Loop). The second-largest art museum in the country hangs masterpieces aplenty, especially Impressionist and Post-Impressionist pieces. Georges Seurat’s pointillist A Sunday on La Grande Jatte is here; so is Grant Wood’s American Gothic. The Modern Wing puts up Picassos and Mirós by the roomful. You'll be gawking for at least few hours.

From the museum’s third-floor sculpture terrace, a silvery pedestrian bridge arches over to Millennium Park. Where to start amid the mod designs? Pritzker Pavilion, Frank Gehry’s swooping silver band shell, around which the park centres? Crown Fountain, Jaume Plensa’s splashy water-work, where video images of locals spout gargoyle-style? Or ‘the Bean’, Anish Kapoor’s 110-ton, silver-drop sculpture? That's the one. Join the masses swarming it to see the skyline reflect.

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Afternoon architecture

Make your way north on Michigan Ave, aka the Magnificent Mile, along which big-name department stores ka-ching in a glittering row. The Tribune Tower (435 N Michigan Ave, Near North) raises its Gothic head on the Mag Mile’s east side soon after you cross the river. Check out chunks of the Taj Mahal, Parthenon and other famous structures embedded in the lower walls.

Across the street, the Wrigley Building (400 N Michigan Ave, Near North) glows as white as the Doublemint Twins' teeth. A few paces north, stairs lead to the underground Billy Goat Tavern (430 N Michigan Ave, Near North). Tribune and Sun-Times reporters have guzzled in the scruffy lair for decades. It's also the place that spawned the Curse of the Cubs. Order a burger and Schlitz, then look around at the newspapered walls, and you’ll get the details.

By late afternoon it's time to get high. The John Hancock Center (875 N Michigan Ave, Gold Coast) is Chicago's third-tallest building, after the Willis Tower (nee Sears) and Trump Tower, but it has the sweetest views thanks to its lakeside locale. Those needing a city history lesson should ascend to the 94th-floor observatory, and get the edifying audio tour that comes with admission. Those secure in their knowledge can shoot straight up to the 96th-floor lounge, where the view is free if you buy a drink.

Evening baseball

Remember the Billy Goat curse? Take the train north to Wrigley Field (1060 W Addison St, Wrigleyville) to see it in action. The ivy-walled, 1914 ballpark is a charmer, despite hosting the woefully hexed Cubs, who've racked up more than 100 years of World Series futility. No tickets? Peek in the ‘knothole’, a garage-door-sized opening on Sheffield Ave, to watch for free. Or practice your swing (and beer drinking) at Sluggers (3540 N Clark St), one of many high-flying bars that circle Wrigley. It's 10 pitches for a dollar at the upstairs batting cages.

If the Cubs aren’t playing, Plan B is to hop the Blue Line train to the Wicker Park neighbourhood. Get off at the Damen stop, and spend the evening poking through hipster record stores, galleries and thrift shops along North, Milwaukee and Division streets. Quimby's (1854 W North Ave) shows the local spirit; the bookstore stocks 'zines and graphic novels, and is a linchpin of Chicago's underground culture. Handlebar (2311 W North Ave) wafts a similar vibe. The bike-messenger hangout dishes eclectic, vegetarian-skewed meals and pours a slurpable craft beer list.

Late-night blues

Grab a cab and finish the night at Buddy Guy’s Legends (700 S Wabash Ave, South Loop). The location is a bit rough around the edges, but the acts consistently smoke the strings. Mr Guy himself plugs in his axe and sings the blues during his January residency.

See? Chicago is your kind of town.

This article was originally published in July 2010. This article was refreshed in August 2012.