
Sure, the shopping in Manhattan is legendary, the food in San Francisco peerless, and we all know the fun never stops in Vegas.
But what about Chicago?
Think of it as a more genteel New York City: a trend-setting foodie town, and more fun than a waterslide in summer. A weekend in Chicago has everything going for it, minus the big-city attitude. From shopping and brunching to caviar facials, this home to celebrities as diverse as Oprah, Michael Jordan and Jerry Springer has something for everyone.
What sets Chicago apart from other Midwestern cities is the cityscape. Famous for its groundbreaking architecture, the Loop area is where the first skyscraper construction took flight—rising from the ashes of the Great Chicago Fire of 1871. The most exceptional example from this period is Daniel H. Burnham's Reliance Building of 1895.
And it just happens to be where my friend Joanna and I are staying.

The 122-room Hotel Burnham now occupying the building bucks the fashion trend by forsaking minimalism and mod lines for marble, mosaics, wrought iron and dark wood trim. This 15-story ode to yesteryear may have begun as one of the world's first skyscrapers, but after a painstaking $27.5 million restoration was completed in 1999, it's now a Chicago-style chic hotel with all the modern amenities.
Dinner offers a taste of why this city has emerged as a culinary hot spot. Walking into Blackbird, on gritty Restaurant Row (a 15-minute walk from the hotel), I'm struck by the contrast of black on white. More specifically, black-clad hipsters sitting in an all-white room. The architecturally sleek Thomas Schlesser-designed restaurant is an elongated space with a streamlined bar, squat tables spaced for excellent eavesdropping, and eerie 7-Eleven lighting. It's pure and simple, the perfect canvas for chef Paul Kahan's award-winning repertoire: French technique married with seasonal Americana.
We dined on a salad of endive, pancetta and a poached egg nestled in a crisp potato nest. The appetizer of sautéed veal sweetbreads with apples, artichokes and black truffles dazzled with its sweet-and-sour apple cider kick. We drank much cabernet with the roasted rack of lamb while chatting with some nice locals (at a neighboring table), who declared Blackbird to be their favorite restaurant in the city. "It always makes for an exciting night out, without breaking the bank," they said.
Great food, excellent service and friendly people who strike up conversation at a swank restaurant. Where else does this happen?
The next part of this story may shock you, for it entails a sort of hazy recollection of consumerism gone mad. But let it be known that a city boasting the Magnificent Mile (shopping and nothing but) is a city that wants you to buy, buy, buy! And so it was that from sunrise to sunset on our second day in Chicago, we shopped like we've never shopped before.
First stop: the Bucktown and Wicker Park area, the spot for starving writers, fueled by jazz bars, coffeehouses and one-off boutiques.
Between 1900 and 1930, tens of thousands of European immigrants, African Americans and rural Midwestern youths came to Chicago in search of work and better social opportunities. Then they cashed in their savings and moved to the 'burbs. Now their art-school educated children are back, giving the area a gutsy avante-garde vibe.
Taking the Blue Line to Damen station leaves you in the thick of things. Head north on Damen Avenue, veer a titch to the east and you're at the stunning Flat Iron Building—88,000 square feet of artists' studios and galleries. Troll Milwaukee Avenue's antique shops, then head to North Avenue's Lille (an excellent gift shop) or Sasabee (for happy bath-time needs). Stitch, on North Damen, is an all-encompassing store in which you might suddenly find yourself in need of anything from a Dutch-made leather wallet to a blown glass vase.
All said, our favorite part was the outdoor platform at the subway station (odd choice in such a cold and windy city), that prompted Joanna and I to cheer in recognition: "E.R.! Chicago Hope!" At least now we were learning there was more to the city than Emmy-winning medical dramas.
Back on the Blue Line (cheap, clean and reliable), we headed to the Magnificent Mile on North Michigan Avenue—a sprawling cityscape of high-end shops and department stores, and a window-shopper's haven.
Using the immensely tall Hancock Tower as our beacon, we pass a 60-person-deep lineup of diehard fans, queuing for caramel corn at the famous Garrett Popcorn Shop. The line is long and the weather is inclement, but the "cornies" are all smiling and chatting. This place is like New York City on Prozac.
We bob in and out of Bloomingdale's, Saks, Origins and Bendel's. We look, we try, we buy. But we bypass the spooky American Girl Place (where pre-pubescent princesses can buy custom-made doll versions of themselves, and dress in matching clothing). I grew up with three brothers, and frankly, this place scares me.
Still, keen to indulge in girlish affairs now and again, I head to the Four Seasons Hotel for a Perle de Caviar facial. A few years ago, the Four Seasons Chicago unveiled its ethereal new Spa & Fitness Center, featuring soundproof treatment rooms, a relaxation room fortified with teas and relaxing daybeds (when I walked in I actually thought a couple of people were in comas)—and some of the best aestheticians in the biz.
My odorless facial used caviar extracts and pearl proteins in the form of creams and scrubs. After the 50-minute treatment, I shuffled over to the relaxation room for more caviar—this time served on toast points, accompanied by a mini bottle of champagne, dahling.

We made reservations for the Four Seasons' Sunday brunch, an annual winner of the Zagat Chicago Survey's "top brunch spot." From the six international food stations, I sampled Peking duck, rack of lamb, seared tuna, shrimp cocktail, homemade granola, crème brulee, fresh omelets and crepes—and that was just my first plate. With more choices than you can conceive of, the suave service and elegant decor merely become excellent extras.
On our last night, we chose carefully for our last meal: One Sixty Blue. Tucked away in an industrial area (currently being reinvented as an extension of Restaurant Row), this renovated warehouse is big and masculine, just like its owner, Chicago's favorite son, Michael Jordan. There's a leathery lounge area at the front, a large humidor to the left, and at center court is a massive open kitchen. We inhaled a fanciful take on a classic winner: duck confit "shepherd's pie," delivered in its own mini casserole dish. The Delmonico steak is chef Martial Noguier's signature dish, and Michael Jordan's favorite meal here.
We topped off the evening with a nightcap at the latest W hotel to open here, another stunning piece of open-concept architecture fueled by midnight revelers lapping up sour-apple martinis. It all seems very New York, but it's better. It's a Midwestern metropolis where the country mouse and city mouse live side by side. And, in fact, are one and the same.
Amy Rosen is the author of Cook This. She writes for numerous publications, including US Weekly, Food & Wine, and the National Post.
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