Cloud Gate sculpture
A Gilded Age mansion
River Architecture Cruise
Stephanie Izard’s Girl and the Goat Restaurant
A pair of pisco sours
A Tiffany glass dome
Chicago’s Millennium Park’s outdoor Performance Stage
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Five days is not nearly enough to see it all in the Windy City

Chicago is infamous for its danger and gangsters like Al Capone and John Dillinger (you can’t scare me, a born and bred New Yorker). But then again, Chicago is also well known for its Magnificent Mile. A fourteen-square-block shoppers paradise. All the usual suspects are here: Armani, Prada, Dolce & Gabbana, Cartier, Tiffany, Tom Ford, Ralph Lauren, Ferragamo, Gucci, Louis Vuitton, and Bulgari. Rounding out these fashionista faves are the glittering emporiums Neiman Marcus, Saks Fifth Avenue and Bloomingdales.

I don’t want to sound blasé about this name-brand nirvana, but remember I lived in Hong Kong for twenty-five years. And besides, I didn’t come here to shop, but rather to walk and eat. So, without missing a step, we power-walked right on by without so much as a backward glance, straight down Michigan Avenue, credit card intact.

Our route took us out along Lake Shore Drive and the mighty Lake Michigan (a Great Lake as big as Britain, literally) to the historic Navy Pier, so named in honour of the WWI sailors who were housed here, and now home to Chicago’s version of the Coney Island Ferris Wheel, a very popular attraction. The Pier also boasts the site of Giordano’s, a constantly packed purveyor of Chicago’s signature gastronomic creation, the Deep-Dish Pizza, where we joined the crowd and pigged out like the rest of them.

We vowed to walk everywhere but heard about the nearby converted warehouse district of Fulton Market with its trendy shops, boutique hotel and hot-and-happening Restaurant Row. We had to check out this vibrant scene, and a Lyft took us there.

Curious about the Star Chef, Stephanie Izard and her string of goat-themed dining establishments, we headed straight to The Girl and the Goat, the first of her group of four (on every Top-Ten $$$$ list). The name alone whets my appetite for a grilled chop or juicy goat burger. No such luck. The menu had just one palatable option. Not an acceptable thick slice of goat country liver pate, but a rather disappointingly meagre goat liver mousse that was paired with an oddly soggy scone. A glutton for punishment, I found myself atop the close-by ultra-hip Hoxton Hotel at Stephanie’s Cabra (goat in Peruvian Spanish) and checked the menu in hopes of finding a mouth-watering array of the Peruvian take on goat. But the single goat here was chopped up and tucked into an empanada, which was heavy on dough, light on goat. Two refreshing frosty pisco sours saved the day. We never got to sample the fare at either The Little Goat or Duck Duck Goat, as both wouldn’t open until later in the evening, and we confined our repasts to early dinners.

In search of the main course and some real food in the neighbourhood, we stumbled upon Publican Quality Meats. I spied through the window a glass case of sausages and salamis. Surprisingly there appeared to be a few tables and chairs. We ventured forth. It couldn’t be more bare-bones in ambience, but my sixth sense (and an enormous aroma from the kitchen) told my nose we had come to the right place. We were rewarded with a big steaming hot bowl of riboletta (day-old minestrone) and a juicy porchetta-filled (deviled pork) bun. Simple but totally authentic Italian food served in humble but honest surroundings. Perhaps I’m just a peasant at heart…and palate.

Another late afternoon walk led us to The Frontera Grill, the first of his many Mexican eateries helmed by Rick Bayless. Our taste buds were primed for his legendary blue corn tortillas. Alas, they were made fresh every day, and blue corn was not yet in season. So, we made do with their limey, spicy seafood ceviche cocktail and washed it down with a couple of excellent mezcal margaritas.

One morning, our doorman told us to try Dublin’s (a nearby dive bar) for the great food and the local color.

So, the next night we took him up on his tip. He was right. It was busy. The bar was crowded with noisy t-shirt-wearing twenty-somethings, and the music was loud. But our scallops were cooked to perfection and came with a huge freshly made, crispy green salad. So much for Michelin Stars.

My Chicago friend from Hong Kong, Margaret, met us at The Drake one evening for their perfect Martinis enhanced even further by the addition of a trio of blue-cheese stuffed olives, a fitting start to an evening that would become the highlight of our time in The Second City: the invitation-only opening reception to Nick Cave’s Retrospective of his fantastical creations at the Museum of Contemporary Art. Just to be walking among the many Cave-filled galleries would be treat enough, but to meet and chat with the man himself made the moment truly magical.

Saving some of Chicago’s best for last — the afternoon before we took off on our trip around the Great Lakes, we checked out Buckingham Fountain (shooting water 150 feet into the air) and walked through Lincoln, Grant, and Millennium Parks until we came upon the enormous (over 60 feet long) mirror-like reflective Cloud Gate, a stainless-steel covered, kidney-bean shaped sculpture by the brilliant Amish Kapoor.

Nearby Frank Gehry’s fanciful outdoor auditorium awaits concert goers. And we made it to the extraordinary Art Institute, with its mind-boggling 300,000 plus works of art. Also, we managed a peek into the Cultural Centre just steps away — couldn’t miss its exceedingly rare pair of swoon-worthy Tiffany glass domes.

Well, one thing is certain. We’re coming back to Chicago.

We’ll spend an entire day at the Art Institute, visit a Jazz Club, see a Shakespearean play, have dinner at the Purple Pig, check out the view from the top of the Willis Tower and visit the Science & Industry and Field Museums.

Text Sandi Butchkiss / Photos Cliff Shaffran