Like many people, I briefly entertained the notion of moving to a new city and starting fresh at the start of the pandemic. Two weeks of sheltering in place had stretched into two months, and the survival horizon seemed bleak. Why not start a fresh, new adventure to mark the start of an apocalyptic era?
“Where to?” remained the question to answer. And then, the thought struck me - what about Chicago?! After all, it is one of my favorite cities in the country. Side step the frowning, focused crowds of New York for the “Paris of the Prairie”! It sounded good to me? My kind of people… people who smile at you - in the words of the late, great crooner Frank Sinatra - and a place with good food, too!
I’ve since cooled on the thought of relocating my life halfway across the country, instead opting for a jaunt by jet to the Midwest to satisfy a whim whenever it may arise. Fortunately, it’s never too long after I leave before Chicago comes tugging at my sleeve by way of an exclusive date travel invitation from a wonderful suitor.
And so it happened that in January, a kind gentleman promised a warm reception if I should be willing to brave the icy temps that come courtesy of a Chicago winter. An alternative arrangement was also proposed and, if I’m being honest, I considered it: as legendarily idyllic as summertime Chi is known to be, winter is just as notable for being exceptionally brutal. But on second thought, I had never experienced mid-winter Chicago and I was feeling up for both a challenge and a change of scenery.
I felt a mix of awe and anxiety as the plane dipped below the clouds, revealing blankets of snow across the expanse of Chicagoland for as far as the eye could see. That snowy cover was replenished later in the evening as we headed out for dinner and sporadically throughout the weekend.
On trips to Chicago, I always choose to stay within the Loop - opting for a high rise location near my favorite shopping destinations on Michigan Avenue or in the amenity-rich River North neighborhood, which boasts easy access to bars and nightlife spots as well as direct access to the lakefront trail for running off the calories in the morning. However, the West Loop has become a focal point of many of my more recent stays. The neighborhood’s explosive growth can almost certainly be credited to the appeal of its authentic Chicago character (even if that character now exists in aesthetics only). The city grew to prominence as industrialization in the 19th and early 20th century created opportunities attractive to both immigrants and African-Americans migrating from the South. The West Loop became an embodiment of this Chicago in both form and function: its gritty character and industrial aesthetic is the footprint created by a diverse community of working class laborers reporting for duty in the warehouses for meatpackers like Philip Armour and Nelson Morris, manufacturers like William Schukraft & Sons, and food producers like Braun & Fitts. Now, in a sign of the times, those same warehouses are home to tech companies like Google, Amazon, Microsoft, and Accenture. The buildings that haven’t been snapped up by tech companies now house art galleries, brand name stores, and trendy, award winning restaurants (some of my favorites in the city!).
Accordingly, this trip became a sort of foodie tour-de-West Loop. The first night, we dined at Viaggio. This nondescript Italian restaurant deserves a description- I couldn’t resist taking fork fulls of calamari which led to me struggling to finish a generous plate of shrimp scampi. I was successful, but had to make a concession and take the cheesecake to go.
It was brave of us to schedule a late night spa date after Italian, but that’s exactly what we did! Aire Ancient Baths is one of my favorite spas in Chicago. It is a major plus that they are open late, when most spas are closed! The Chicago location occupies a cavernous space in a former factory, which smartly combines the building’s original features with exposed brick, candlelight, and ambient lighting that evokes the feel of an ancient bathhouse. The generous square footage - nearly 20,000 - makes for a near-private feel as you navigate six pools and two steam rooms in whatever sequence you choose. One unique aspect of our visit was that we were able to enjoy one of the heated baths while the snow fell on our heads and shoulders… kissing in the steam and snow made for a romantic scene, much like being in a movie!
Our weekend was, in fact, a movie. Dare I say it was a masterpiece? When it comes to film, art, food, or dates, the difference between good and exceptional is in the details. Some people are exceptionally attenuated to them - and it was apparent in my date’s thoughtful planning of every detail of our weekend together. When we pulled into the Grand Geneva Resort & Spa for a brief overnight escape from the city, our bags were unloaded from the car by the bellmen while we were ushered inside our gorgeous villa. Stepping into the foyer, we were greeted by an en-suite dinner set up and a duo of masseuses who had already set up for a romantic couple’s massage.
The property sits on 1,300 acres, secluded in a wooded area a bit uphill from Lake Geneva. But access to the town is not a problem: we woke up late the next morning and drove down to Oakfire for lunch with an incredible view of the frozen lake. I actually had been enjoying the winter weather and snowy landscape, but that moment was probably the only time during the trip that I felt an intense longing for summer!
When we arrived back in the city, it was snowing again. This made for the perfect excuse to be languorous without feeling guilt! What I can appreciate about the Chicago winter is that there is not much to do besides indulging in some of my favorite activities: shop, sleep, and eat! [And another s word :-)]. Between episodes of shopping and hibernating in between high thread count sheets, we spent most of our time eating at some of the best restaurants in the city. Boka Restaurant Group has been behind several of my favorite Chicago restaurants (Boka, Girl & The Goat), which heightened my anticipation of experiencing the restaurant group’s steak concept Swift & Sons. It proved well worth being excited about! The tartare was some of the freshest tasting steak I’ve ever had, with nuanced anchovy and roasted garlic flavors. It was served blanketed in a snow-like covering of bandaged cheddar, and almost too beautiful to eat. The Beef Wellington, however, was the true highlight of our meal. It is wheeled out on a carving table, like a work of art it is: the outer layer is a perfect, flakey pastry embossed with a cow. It almost hurt to see the server pierce it with the knife! A cute dessert cart concluded our service… but the real dessert was to be had elsewhere.
On the eve of my departure, we crossed another Nobu off my bucket list. Long ago, before I knew of Michelin and OAD lists, I thought of Nobu as the fanciest that a fancy restaurant could ever be. I therefore made it a goal to visit every one of their locations in the world. The Nobu in Chicago opened mid-pandemic on restaurant row - which is, of course, in the West Loop (clearly, an ambitious bet on the future prospects of the neighborhood). The downstairs portion of the restaurant seems to sprawl out in every direction and utilizes the classic minimalist color palette and aesthetic. We ate upstairs in the rooftop space, which evokes more of a nightclub feel with dark mood lighting, intimate lounge furnishings, and a DJ set up. The rooftop dining menu is separate from the traditional menu; it has a few classics, like the jalapeño yellowtail and rock shrimp, and other delectable finger foods unique to this location. The Nobu style fish and chips and ribeye sliders stuck out to me as most memorable.
After dinner, we walked through Navy Pier to grab a warm espresso and hot chocolate as a digestif. Warmth in hand, hand in hand, we admired the glistening stillness of Lake Michigan while walking north on the Lakefront Trail towards our hotel. We both agreed that it had turned out to be a wonderful trip, although it initially seemed we wouldn’t have much to do. But it always turns out to be that way: a wonderful date only requires me and you.
No matter the destination, the season, or the weather - I can be available for you whenever! Travel is one of my first loves, and I’ve found that every visit brings out something new to discover about a place whether it is the first time or the fifteenth. I am available for day dates, overnights, and even extended domestic or international trips. Whether I’m coming to you or with you, it’s always a pleasure. Reach out and let’s make plans!