The first day actually began en la noche as I departed to O'Hare for my 1 a.m. flight on Aeromexico. I was initially apprehensive about the flight's timing, until I realized—night owl that I tend to be—that getting there so early would afford me an entire day of leisure. And never has a complimentary cocktail on a flight been so well-needed. Muchas gracias, Aeromexico!

After a three-and-a-half hour flight (yes, you read that right), I arrived to a still-darkened Mexico City. By 5:30, I had made it to the W Mexico City (www.starwoodhotels.com/whotels&; in the ritzy Polanco neighborhood. I was a bit woozy from the unusual travel time and when the gentleman at the check-in desk asked me four times if I wanted "one key for my room," I could swear he was asking if I wanted "Joaquina for my room." I don't have much use for a Joaquin at this hour, much less a Joaquina, I thought to myself before the idiot cloud passed, I accepted Joaquina (which was the name I assigned to my room key), and headed up to the 16th floor.

I entered my room and was immediately enraptured by the view of the endless landscape of city lights, which I drank in slowly while resting in the hammock which was strung diagonally across the shower room. The entire exterior wall was a window and it peered right into the heart of the massive, bustling metropolis. It was a worthy introduction to the city.

I slept until noon, napped until 2, and then struck out into the city, in search of culture, comida, and a better deal than the 152-peso single-shot bottle of vodka in the honor bar.

I was impressed with the public spaces of the city. Sculpture, both sparklingly new and quaintly crumbling, dotted the green spaces nestled between the buzzing avenues. As I got strategically lost among the foreign embassies and Spanish-tiled private residences of Mexico City's most upscale area, I pondered the contrasts of the city. Like Chicago, Mexico City has strived recently to shake off the stigma of a gritty past and to shine as an improved, safer center of commerce and high living. Crowded buses with broken windows zoomed past, hinting at a stark economic range typical to any large world city.

And I found a much larger bottle of Smirnoff for 158 pesos, but more on that later.

That evening, I began what was to become a quasi-intimate relationship with the food of Mexico City. I dined with utter delight at Pujol (www.pujol.com .mx), voted one of the world's 50 best restaurants by San Pellegrino. He appeared at first to be out of my league. Then he tempted me with his ant larvae tostada with kohlrabi and leek. By the time I had his dessert with mango mousse, passion fruit, grated macadamia nut and coconut gel, I was putty in his hands.

Now that I was just so much putty, it was time for a drink. Word from the locals led us to Marrakesh (Republica de Cuba 23). We were warned that it was in a "bad part of town," but as everyone in my group was either from Chicago, New York or Washington, D.C., we didn't much wither at the warning. While Nicki Minaj boomed from the sumptuous sound system, a rotating cast of daring youth danced on the bar while cheesy '70s Mexican soft-core porn was projected on the large wall over the dance floor. Drink prices were spectacular—at least for me. I paid 20 pesos for a Dos Equis, while another in my group who was not so melanin-rich paid considerably more. Just speak Spanish and you'll be okay. And if you don't think you speak Spanish and you're coming from Chicago, trust me, you speak Spanish. It'll just come out after about quatro or seis Equis.

El dia numero dos:

I began my day in a hot, passionate romp with a plate of chilaquiles verdes from W room service. When I was finished, I wiped my face (because I'm a lady) and traveled to Carcamo in Chapultepec Park. This newly-restored, mosaic-tiled fountain serves as the ceremonial entrance of the water of the Lerma River into the city. Directly behind the fountain is a cistern which is brilliantly painted with "El Agua, Origen de la Vida," a mural by famed Mexican painter Diego Rivera. The marriage of the engineering feat of the Carcamo water source and the emotionally jarring Rivera mural speaks to the attitude of a city which has grown and innovated to astounding proportions, while keeping in mind its cultural and historical beauty.

The Monumento a la Revolucion (www.mrm.mx) stands as a proud beacon of remembrance of Mexico's storied revolution, which began in 1910. Originally the centerpiece of an entire federal legislative palace designed by French architect Emile Benard, it was the only building begun before the government funneled funds away from the project to fight the revolutionaries. For two decades, it stood an unfinished steel structure, until Mexican architect Carlos Obregon Santacilia overtook the project, declaring it a monument "to the revolution of yesterday, today, tomorrow, and always." The basement houses a museum of the revolution and the observation desk provides some stunning views of the city.

I then continued my culinary affair at Azul Historico (www.azulhistorico.com), where chef Ricardo Muñoz Zurita warmed me up with a shot of chicken breast mezcal served in a carved jicara shell. He then ravaged me with in-season poblano peppers, stuffed with a sweet melange of fruit and rice and drizzled with a sweet/sour duo of white sauces and sprinkled with pomegranate seeds. When I thought I could take no more, the Tres Leches dessert sent me off in ecstasy. Not feeling a drop of self-consciousness seated among Mexico City's fashion elite and boozy businessmen, I then had a cigarette and did a little shopping. You know, just to come down a little.

In an educational effort to walk off the decadence of Azul Historico, I headed to Templo Mayor, the ruins of an Aztec temple discovered 35 years ago when electrical workers found a stone monolith while digging. Templo Mayor provides a shocking link to the past, when warriors and human sacrifice were de rigueur in pre-Hispanic times. My favorite moment at the Museo del Templo Mayor (www.templomayor.inah.gob.mx) was seeing the "face knives," anthropomorphically-decorated knives which, upon initial glance, provide a goofy grin. Then, once you realize their connection to human sacrifice, you ain't grinning so much.

Back at the W, I was shown some of the amenities of the hotel in a far more grand fashion than I was expecting. Tequila shots, breathtaking views of the night skyline and mariachi bands concealed in circular showers were just a few of the bells and whistles that trumpeted the W as the place to stay in Mexico City.

Hong Kong's DJ Angus Wong spun all night at Whiskey Bar, located in the lobby of the W, and after the previous night at Marrakesh, that was as far as I went. Kirk out.

El dia numero tres:

My fling with the W's chilaquiles verdes proved to be a two-morning stand. He bade me farewell and I ran into the morning and ultimately to the Museo Universitario de Arte Contemporaneo (www.muac.unam.mx). Part of the university system of Mexico City, MUAC held the fist public collection of contemporary art in the country. The exhibits highlight a strong connection to education of the form and interactivity with the patrons. La Selva Sintetica (Synthetic Jungle) from artist Jorge Alberto Alba floods the senses with individually-generated, simulated sounds of the rainforest that combine and crescendo into a hypnotizing soundscape. In another room, signs inscribed with sayings—both witty and dire—litter the floor and walls and encourage the public to play with the labels and to act out, in direct opposition to how we are normally taught to behave in museums. It will bring out the child (and the artist) in you.

The next stop was Bazar del Sabado San Angel, a huge bazaar where you can find gorgeous textiles, tchotchkes in every color of the rainbow and tequila, tequila, tequila! It skews a bit touristy, but it's a worthwhile stop to spend a few pesos on some authentic keepsakes of your trip. I'm kind of obsessed with the Day of the Dead skeleton shadow boxes I found and I'm kind of wishing I'd bought twenty instead of three, which at 50 pesos a piece would have been a reasonable transaction.

A brief walk from the bazaar was lunch at Paxia (www.danielovadia.com .mx/vExplorer), another jewel in the fine dining crown of Mexico City, where my love spree continued. The black mole sauce that came with the "Quesadillas Oaxaca" was certainly marriage material, and I can't wait to introduce it to my mother. The honey-glazed sweetbreads turned out to be a bit of a Monet unfortunately; it looked sexy and inviting on the plate, but turned into just so much fat in my mouth.

One cannot forget that Frida Kahlo was a native daughter of Mexico City. Her face was emblazoned on half the tchotchkes at the bazaar! It was a fait accompli that I would end up at Frida and husband Diego Rivera's house and studio for a look-see. Sadly, I was too late for a look-see, but had a nice look-buy at the gift shop. My Frida Kahlo shot glass was broken in almost immediately, thanks to a small bottle of tequila I snagged at the bazaar.

I stopped back to the W to freshen up (read: nap) and almost drifted off to sleep when a knock came at the door. A complimentary glass of champagne from the W as a final gift. Class, baby. As I stood naked in the shower with my champagne and looked out one last time over the city lights, I choked up just a little, realizing it might be a while before I get this glamorous again. All things must pass ... .

Time for one last fling at Bar Tomate (www.grupotragaluz.com/rest-tomate_mexico.php&. He got a little "fresh" with me, but I certainly did not mind. After the upscale experiences at Paxia and Pujol, I reveled in the simple, hearty, bistro-like atmosphere of Bar Tomate. The exquisitely spiced tuna tartare made my night. I'll always remember you, Bar Tomate, as the one who got away.

The trip was rapidly coming to an end as I flew out early the next morning, but the group and I endeavored over to Living (www.living.com .mx) for one last hurrah. Living bills itself as the ultimate gay club and it has the decor and talented DJs to prove it. Regrettably, due to a migraine brought on by the tannins in the wine at Bar Tomate (which is no assault on Bar Tomate, but an unfortunate reaction I have to wine in general), I was not living for Living, and as my 9 a.m. flight loomed, I bade a fond adios to the group and headed back to the W for precious little sleep.

El dia numero quatro:

Near-heart-attack-inducing wake-up call; silent shuttle to the airport; "Donde esta la puerta numero sesenta y dos?"; brief airborne nap; few episodes of Shameless on my iPod; unopened bottle of Smirnoff through customs; home by early afternoon.

See www.visitmexico.com/en-i0/mexico-city to plan your own trip. Photos by Kirk Williamson, except where otherwise indicated.