Chicago's got glamour, notoriety and great restaurants

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From the outside, 1520 North Damen Ave. looks like just another abandoned building. Its façade is boarded up with weathered strips of wood. A graffiti-like motif covers the area where shop windows might have been. But at night, there are signs there's more here than meets the eye.

The first clue is the line stretching halfway down the block of people waiting to get inside. The second is a single, glowing, naked light bulb – the signal that this speakeasy-style bar is open for business.

On a recent visit, I am ushered through the concealed front entrance by a gracious doorman, who pushes aside a set of heavy curtains to reveal the beautiful, gleaming cocktail bar that is The Violet Hour. In sharp contrast with its dingy exterior are soothing powder-blue walls, chandeliers and glowing candles, and a row of bartenders clad in neckties, busily assembling drinks behind a polished bar. It's easy to understand why GQ magazine named The Violet Hour one of the best cocktail bars in America last year.

I gape. I take a seat. And I order what is possibly one of the most delicious cocktails I've ever tasted – The Violet Hour Old Fashioned, a mix of bourbon, demerara syrup and Angostura bitters, served with a slice of orange rind.

Glamour and grunge collide in unusual ways in Chicago. The twinning of opulence and seediness are practically a part of the city's DNA, and the fun lies in seeking out a balance of both.

"We certainly are blessed culturally," Chicago historian Richard Lindberg says about the city's museums, art galleries, theatres and festivals. "But I would argue that Chicago is the sum total of its parts. It is a city that blends the glamorous with the notorious."

Mr. Lindberg would know. He has written multiple books on the Windy City's colourful past, and leads annual fall tours of its historic underbelly, organized by the Chicago History Museum. Since its early days, he says, Chicago has attracted great wealth – and those in search of it – because of its location in the industrial heartland of the American Midwest. It's a city shaped as much by the elite as by gamblers, Prohibition-era booze smugglers, gangsters and the downtrodden.

"It's all a part of the history and fabric of the city," he says.

And you needn't look hard to find evidence of Chicago's seamy side.

On the first morning of my visit, while having breakfast at the swanky Sixteen restaurant in the Trump International Hotel and Tower, my attention is drawn to the neighbouring landmark Jewelers' Building, within full view from the restaurant balcony. Constructed in the 1920s as an office tower, the building is a handsome work of architecture, with elaborate domes and spires. But arguably, its most fascinating features are its now-defunct, automobile elevators, originally installed to deter curbside jewel heists. The building's top level is also rumoured to have once served as a speakeasy for notorious crime boss Al Capone.

The clashing dynamics of the city's highs and lows aren't just found in the remnants of its past but in its vibrant, up-and-coming neighbourhoods. Leaving the Magnificent Mile behind, I descend into the nearest subway station and catch a connecting train to the Blue Line "L," the elevated rapid-transit system.

Chicago's public transit is incredibly visitor-friendly. A $14 (U.S.) pass allows you to take unlimited rides for three days to all corners of the city, and the train system is easy to navigate. I take the L northwest to the eclectic area where Bucktown and Wicker Park meet. The dividing line between these two neighbourhoods is a former working-class area that in recent years has become a must-visit hot spot. It's the Chicago equivalent of Vancouver's Main Street or the Ossington strip of downtown Toronto. Despite its gentrification, Bucktown-Wicker Park still retains some of its rougher edges. Trendy cafés, bars, vintage stores and boutiques can be found among run-down laundromats and smoke shops.

If the high-end brands like Louis Vuitton and Burberry on North Michigan Avenue aren't your style, take a walk along West Division Street in Wicker Park, between North Damen Avenue and North Milwaukee Avenue, where you'll find plenty of cool shops that carry independent labels, one-of-a-kind items and arty homeware. And if you get hungry and weary, head over to Big Star, a taco joint and whisky bar, located in a space that appears to be a revamped auto-body shop. Big Star is directly across from The Violet Hour, and it's much more conspicuous. It's practically impossible not to feel uplifted by the boisterous atmosphere, old-school rock 'n' roll spun on a turntable, and crispy beer-battered fish tacos.

My next destination is the West Loop. This area of Chicago has also rapidly changed over the years from a gritty warehouse district to restaurant central. Here, you'll find some of the city's most buzz-worthy dining establishments, such as The Publican, Moto and renowned chef Grant Achatz's constantly changing Next restaurant.

I make a beeline to Girl & the Goat, a restaurant that has garnered plenty of publicity since it opened last year. Reservations are hard to come by, especially on short notice, so I find a seat at the crowded restaurant lounge. Upon reading the menu of intriguing dishes, like confit goat belly and fried stingray, I'm willing to believe the hype. I order a plate of pan-fried duck tongues, topped with slices of pickled watermelon rind, and a serving of sweet and sour cod cheeks, with bacon, potato aioli and tempura broccoli. Within the first bites, I'm sold.

The couple sitting next to me are clearly enjoying their dinner too. And it's not long before we're swapping tastes of each other's dishes, all of which are perfect for sharing, after all. Everything I try is insanely good.

I stumble away stuffed and satisfied, and desperate to work off some of the calories I've just accumulated. So I head back in the direction I started from, to Millennium Park, where the outdoor ice rink has just opened for the winter. I rent a pair skates, step out onto the ice and join a swarm of people, young and old, from all backgrounds, laughing, gliding and bumping into one another. It's hard to imagine a happier place.

The Insider: chef Stephanie Izard

Here's how chef Stephanie Izard of Girl & the Goat would explore Chicago:

"I would spend my day visiting the Shedd Aquarium and Museum of Science and Industry. … The aquarium [1200 South Lake Shore Dr.; sheddaquarium.org] is awesome. It has a great newer shark exhibit and is a great place to go on a weekday when it's not too crowded. The Museum of Science and Industry [57th Street and Lake Shore Drive; msichicago.org]is fun because there are so many hands-on exhibits. …

"I also like doing a little shopping in the Wicker Park area. Wicker Park is an eclectic area with some high-end boutiques and some funkier local shops. …

"Avec [615 West Randolph St.; avecrestaurant.com] is my favourite place to get some snacks and wine in the city. They offer wonderful small plates to share in a casual atmosphere with great wines. It is the perfect place to stop in around 4:30, before the restaurant gets too busy."

As told to Wency Leung