The guy at the mike, Len, is coaxing a young woman onto the stage with teasing, improvised lyrics in a voice that sounds like it’s been dragged around the block.

I’m taking in amateur night at the Kingston Mines (2548 N. Halsted St.), a blues stronghold in Chi-Town for more than 40 years. It’s been well over a decade since I first visited this seductive hovel, and save for the absence of a thick cloud of smoke, it hasn’t changed a bit — same orange ceilings, same bench-style tables and mismatched chairs, same music borne of heartache that engulfs the souls of those who hit the two stages each night.

Tonight, the star attraction is Len, who keeps talking about how much pot he has smoked, and who grinds out songs of regret and missed sexual opportunities with a young babe in hopes that said young babe will join in the musical banter. She does, and for a song or two it works. Luckily, they have a strong guitarist backing them up.

Back at the sleek, contemporary W Chicago Lakeshore Hotel (644 N. Lake Shore Dr.), my husband and I walk past the outdoor “living room” that greets us upon arrival and take the elevator up to our floor, where the doors open to large windows overlooking a stunning view of Lake Michigan and Navy Pier. Once ensconced in our room, however, I am dismayed by the lack of a solid wall between the bed and the bathroom, which is a scant three feet away in an already tiny room. The flimsy shutters covering the large cutout in the wall and doorway offer little privacy for prepping for the first weekend without the kids in months. (All is forgiven, however, with my first sip of a mango mint mojito, taken with a side of truffle fries in the hotel’s way-cool Living Room Bar.)

The next morning, we make our way through the lobby, where club music, dim lights and beautiful people lounging everywhere create a non-stop party vibe, and hit the streets on foot. We find ourselves engulfed by beauty at every turn. Chicago’s architecture is legendary — the Sears Tower (now the Willis Tower) was the world’s tallest building when it was built in 1973, and still stands as the tallest building in North America. World-famous architects Ludwig Mies van der Rohe, Helmut Jahn and firm Skidmore Owings & Merrill all left their mark here. The seamless melding of historic buildings and modern structures is nothing short of remarkable.

With The Magnificent Mile (the portion of North Michigan Avenue from the Chicago River to Oak Street) stretched out before me, I proceed to fondle seemingly every garment at Bloomingdale’s and Neiman Marcus, when I’m not drooling over the bling at Cartier and other high-end shops. While I’m smitten, my gasping wallet reminds me The Magnificent Mile was so named because it’s one of the city’s most prestigious residential and commercial thoroughfares.

It isn’t until we finally take a rest stop at Argo Tea, that I realize how ravenous I am.

A substantial scone and chai later, we limp back to the hotel to take advantage of a free ride (wherever W guests want to go, within a 5-mile radius of the hotel), courtesy of a promotion with Acura. The driver, who looks and sounds like a metal-toothed baddie from a James Bond movie, also acts as tour guide. He explains that Chicago is made up of pockets of “activity,” with large areas of seedy or nearly deserted areas in between. As the lights of the last pocket disappear behind us on our one-way trip, I’m grateful we budgeted for a cab ride back (US$10), instead of relying on our usual penchant for transit.

Whenever I’m in the States, I head to the closest Mexican restaurant, and Las Fuentes Restaurant (2558 N. Halsted St.) is about as authentic as I’ve seen. I’m a big fan of mole of any kind, and the pumpkin seed mole chicken fails to disappoint. My husband goes for the Borrego en Mole Negro, a New Zealand rack of baby lamb in classic Oaxacan black mole. The house specialty is enchiladas, but we can’t see past the myriad mole options and vow to try the Pollo en Manchamanteles (Amish chicken breast in nut-thickened Mole Poblano with chorizo, pineapple and plantains) on our next visit.

The next morning, we head straight to Millennium Park (N. Michigan Ave. and E. Randolph Street), all 24.5 acres of it, and are immediately drawn to Crown Fountain, designed by artist Jaume Plensa. The fountain is composed of a black granite reflecting pool between a pair of 50-foot glass brick towers. Digital videos display the faces of locals on the inward facing walls and weather permitting (from April to October), water cascades down the two towers and spouts through a nozzle on each tower’s front face. With a price tag of US$17 million, the faces of those around us tell us it was worth every penny.

And the Cloud Gate sculpture, an enormous reflective “bean,” makes me positively giddy. The sculptures, the ambience and structures like the 925-foot winding BP Bridge give us ample reason to linger in Millennium Park until it’s time to catch our train from downtown to the airport.

Seventeen stops and an hour later on CTA for just US$2.25, we arrive at the airport with just enough time to tuck into an Auntie Anne’s sublime garlic pretzel with sweet marinara. It proves a perfect send-off from Chi-town — salty, saucy, rich. And leaves me wanting more.

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