The Long Way Home

There is no place like home. That said, there is something to be said for exploring.

This time the road took us to the Great White City. Chicago is a place I rarely tire of, though I will admit I have never had to reckon with the winter, or with the bluster coming off Lake Michigan.

Our home for the Chicago leg was the Chicago Athletic Association, once a private club, since rescued and reborn as a luxury hotel with every nod to its 1893 origins intact. The neo-Gothic interior is an architectural marvel in its own right, cozy but brooding and dark, a tribute to the Doge's Palace in Venice. Monica and I have both done Chicago before, but never together, so this was a chance to play tourist.

First up: Buddy Guy's 90th birthday show at the historic Chicago Theatre. A living legend. As someone who once saw Chuck Berry in his eighties and took consolation in the flashes of brilliance that surfaced, I had checked my expectations. Those expectations were misplaced. At 90, Buddy is still rocking the Delta blues, the notes pouring out of his fingertips and the voice coming straight from his soul. From there we made our way to Pops for Champagne to meet our dear friend Jessica Stiver, the bubbles and the reunion doing their work, and raised a toast to the night before heading off to rest.

The following day, sightseeing on the river. Chicago is an architectural wonder, and while anyone with eyes can see that for themselves, the reasons behind it are more circumstantial. From the ashes of the Great Chicago Fire came that quintessential American pioneering spirit to rebuild, drawing architects from all over as the city dared to reinvent itself. The Beaux-Arts style is something I have always appreciated, and for all its march of progress, Chicago is a city that has honored its heritage well. From the cantilever bridges to the towers and hotels reimagined but kept whole, it is a rare trait in America. Coming from the greater New York area and living in Houston, I can tell you heritage is rarely revered like this.

In that same spirit of culture, I set out to remedy a great gap in Monica's life: she had never had a real Italian beef. For fans of The Bear, and for someone baptized in the tradition at Portillo's once upon a time, I wanted to do it right. I feel like I missed the mark showing Monica her first Philly cheesesteak, so I was determined not to repeat the crime. We split one done properly at Bongiorno's Cucina Italiana & Pizzeria. I am sure some locals will challenge me, but this was excellent, a communion with the food gods just short of a sacrament, the kind whose memory lingers long after the last bite. Crispy and chewy roll soaked in jus, spiced beef, the meaty gooey richness of provolone kissed by the flames of a 600-degree broiler. What is left to say?

Touring the towers has a way of making you thirsty. We found the top of LondonHouse, a summer day and the spot everyone insists you have to hit, and it was a bit of a miss. No mint meant no mojito, and honestly the crowd was more about the gram than the experience. We tried our luck at the Wit, which has a lovely rooftop, only to be turned away for a private event. Third time is the charm. Back at our base of operations, we made our way up to the thirteenth floor of the Chicago Athletic Association to Cindy's, facing the lake. Beautiful. The wharf-and-fisherman theme was fitting, given we were packed in like sardines. After a hot day we angled for the bar, Monica taking an open seat and me commandeering its neighbor the moment a couple left. Success. The mojito was among the best in memory. I do not drink liquor often, but when I do it makes me appreciate a great bartender, and this man hit the mark. Monica leaned in for a favorite that sounds common but is not: a truly great extra-dirty gin martini is hard to find, and find it she did. Throw in the blue cheese olives and, well.

Dinner was on the agenda: RL, the Ralph Lauren restaurant, which is like walking straight into a Ralph Lauren spread, all rustic Americana. The dining crowd was eclectic. At the table across from us, a woman informed her two hosts that she is normally a six but a Chicago ten. We shared a half chicken, and call it sacrilege, but a bottle of PlumpJack to go with it. We finished that and then it was off to a wild-card night. The plan had been some North Side haunts with history, but we found ourselves at live-band karaoke instead, where I was briefly employed as the house band's singer. The pay came in compliments and free drinks from fans who would forget me by sunrise. But Monica, my number one, will bring that energy any time there is a microphone and a stage.

The next morning we allowed ourselves the luxury of no alarm. An overcast day, the Willis Tower all but invisible from our second room at the Chicago Athletic Association, this after the poop-water debacle of our first night there. The day's task was cultural: Oak Park, and Frank Lloyd Wright's home and studio. It was scorching, the sun blinding, and our guide Margaret gave us the best kind of tour, one that felt more like a conversation than a script. We took in the intricacy and intention of Wright's designs and learned a thing or two about the mentors and predecessors whose work is scattered throughout Chicago. Then the sun gave way to ominous skies, and we ducked into a deli for lunch as the rain came, our Uber driver running a stop sign and my life flashing briefly before my eyes as we were nearly t-boned. A turkey club hit the mood right; Monica took a patty melt. It is clear the locals are the primary audience here, and that is exactly what I love about it. The sky went darker, the lights came on as if it were night, the wind kicked up, and then the tension broke into torrential rain. It flooded into the restaurant bathroom as I went to wash my hands. We made for Unity Temple during a break, but the rain was not finished. In a moment of irony, or maybe parallel, we watched waterfalls pour down the steps of the Unitarian temple. Soaked through, I checked the entrance and came back for Monica. We walked into a scene in crisis: the rain so intense that the toilets in the church basement were overflowing. Well, Frank. There is something you did not think of. We toured ourselves through it and took it in, truly unique and still in active use.

The rain let up and we braved it to the Uber, back to the hotel to reset. We changed and walked the two blocks to the Art Institute of Chicago, past the bronze lions standing guard in the wet. I had never once stopped in on my earlier trips, always a meeting, always an excuse, and yes, I had been missing something. It is a place that humbles you by the room. You round a corner expecting a hallway and instead there is Caillebotte's rain-slicked Paris intersection the size of a wall, and past it the Impressionists hung three deep, and the Americans in their own hushed rooms, Hopper's late-night diner glowing to nobody, Grant Wood's farm couple staring you down with a century of Midwestern suspicion. You could give it a day and not finish. We had an hour and the weather on our heels.

As we wandered the galleries, we caught another dark front building out over the lake. Monica made the call to leave a little early, and we walked briskly back to the hotel trying to beat it. The radar showed something mean; the wind came up; and almost the instant we crossed the threshold, a clap of thunder and the sky let go. We settled into the lobby bar in a cozy seat by the window and watched it come down, a glass of Champagne and a glass of wine between us, the storm doing all the entertaining. Once it cleared we dressed and went to Copa di Vida for dinner. Succulent and delicious, the right kind of quiet after a loud sky.

No agenda the next morning, so we took it slow. Then we picked up the car, Lake Geneva, Wisconsin on the itinerary for Monica's week, and on the way we rolled past the Home Alone house. Campy, touristy, sure. But why not? A quick photo, a little respect for the neighbors, and on we went.

Lake Geneva is beautiful in that hushed, moneyed way, quiet and picturesque, a town that was once the summer refuge of Chicago's elite and, from the look of the boathouses, may still be. Monica was there for a conference. I set up remote and worked with partners on a few things we are weighing, but the highlight for me was a meeting with Daniel Ammann. For those who do not know, Daniel wrote King of Oil, a book about one of the most underappreciated and controversial figures of the twentieth century, a man most people have never heard of. The commodity market for oil? He basically invented it. I am working on an industry business book of my own and wanted his perspective as the project advances. He was generous with his time, from Switzerland, while I sat in Lake Geneva, Wisconsin. How is that for coincidence? Afterward I walked the length of the downtown, took a slow lunch, and got back to work and writing, breaking only for a ride out on the water as the sun went down and turned the lake to hammered copper.

Then, Milwaukee.

Why Milwaukee? Why not. I had never been, and it was good. We rolled in during the afternoon and pulled up to the Pfister, the Grand Hotel of the West when it opened in 1893 and the Grande Dame of the city ever since, from an era when they still built hotels like cathedrals. The three-story lobby stops you at the door, a sweep of marble staircase and a fireplace you could nearly stand in, the walls carrying the largest collection of Victorian art in any hotel in the world, two bronze lions keeping watch over all of it. Guido Pfister, a German immigrant who made his fortune in leather, wanted a palace for the people, and he built one. We dropped our things and made for the park, where a live blues show was already going. The bartenders were volunteers, borrowed for the night from local restaurants, and Casey, the one who drew my order, had no earthly idea about the show, the beers on offer, or what any of it cost. He rang me up with the cheerful helplessness of a man who had wandered into the wrong job an hour before. The quaintness of it. We carried our beers into the crowd, let the band work a while, then wandered up the block to the Milwaukee Art Museum.

I will be honest, I did not expect much, and the building corrected me before I was even inside. That great white Calatrava pavilion out on the lakefront, the one with the wings, the brise-soleil that opens and folds over the glass hall like something breathing. Not every museum is going to be the Met or the Guggenheim, but I have learned that some of the regional ones will surprise you. Earlier this year I stood in front of Girl with a Pearl Earring at the Mauritshuis in The Hague, a small collection that punches far above its size, and Milwaukee has that same quality, the kind of place where you slow down and actually look. We took our time, then walked back to the Pfister to freshen up before our eight o'clock reservation.

Alina, the Spanish room tucked along the main drag, has clearly put money and thought into what comes out of its kitchen. It is good. Not good in the way every Iberian place is good, the same tapas photocopied down the block, but good in the way that tastes like one chef's actual soul and mileage. Service was polite, the wine list robust but disciplined rather than showing off, and the value honest. We put ourselves in the hands of that list and opened a bottle we would not have found on our own. To keep it a little healthier we ordered lean and shared, which is also the trick to tasting more of a menu. The standout was the Spanish brisket, the chef's cut, an almost-chorizo note running through it, smoke without heaviness, a dish that knew when to stop. The owner made his rounds, the sort of sociable, genuinely warm host who makes a dining room feel like his living room, and we walked out full and happy.

We passed a few bars on the way back but climbed instead to Blu, the sky bar twenty-three stories up in the hotel's 1960s tower, the city laid out beneath the glass. Clearly the place to be. We went with a Greenwing by Duckhorn, a bottle that drinks well above its price, and I will always trust a winemaker with a name to protect not to put out something embarrassing under it. One glass in, the main bar downstairs was hitting its stride, a wedding the next night, a class reunion already loud, the whole building leaning into its Saturday. We took the show back to our room instead. It had been a long day, and there is a particular luxury in choosing the quiet.

The next day came in gray and wet, no agenda beyond reclaiming the sleep the road never quite lets you keep. We found a local place with good reviews, and behold, our waiter was Casey, the same beautifully clueless volunteer from the park the night before, or his exact twin. I have decided not to investigate. We shared a grilled chicken sandwich, an easy lunch, and then set out for the thing I had circled on the whole trip: the Pabst Mansion.

I had bought tickets weeks ahead, though I suspect the crowds do not exactly storm the gates. A preservation group rescued the house from the Archdiocese of Milwaukee back in the seventies and has been patiently putting it back together ever since, room by room, and the rain only deepened the mood of the place, another survivor of that 1893 world. The house is a Gilded Age argument in stone and carved wood, ornate to the last hinge, and every inch of it makes the same case: a man built this to show how far he had come. Frederick Pabst landed in this country as a boy in 1848, settled first in Chicago, and made his early living on the steamships of the Great Lakes, working his way up the decks until the title stuck for good. He was always the Captain. Brewing was the second act, entered only through his father-in-law, Philip Best, whose small Milwaukee brewery Pabst joined in 1863 and would one day grow into one of the largest in the country. He was good on the boats. He turned out to be better at beer. The mansion is the manifestation of all of it, the brewery, the fortune, the place he and his wife finally settled into late in life. And here is the part I love. Pabst was as much marketer as brewer. Beginning in the 1880s, to flag the awards his beer kept collecting, he had a length of blue silk ribbon tied around the neck of every bottle, not a prize won but a signal sent, a thing customers learned to point at and ask for by name. Then came the 1893 World's Fair right down in Chicago, where he built a terra-cotta booth trimmed in gold leaf and his beer took a top prize, and the story everyone tells traces the name to that afternoon. The company made it official at the century's end. Pabst Blue Ribbon, born of one deliberate flourish that rewrote a fortune.

From there we found the old watering hole, a former Schlitz tavern gone comfortably to seed, the kind of dive where you can catch the faint ghost of last night's shame somewhere in today's mop bucket, and yet the welcome is warm and the people are exactly who they say they are. They tried hard to sell us on their kitchen, but we had bigger designs on the evening.

We were headed for a true Midwest supper club. The Five O'Clock Steakhouse, Coerper's Five O'Clock Club in an earlier life, has held down its corner of Milwaukee since 1946, and walking in is like stepping onto a set dressed for Goodfellas: low light, dark wood, the low murmur of a room that has seen everybody. There is a ritual to it, and you do not rush it. They meet you at the bar and pour while a waiter quietly readies your table, a relish tray waiting when you sit down, and you go along for the ride. An old-fashioned with rye for me, an extra-dirty gin martini with blue cheese olives for Monica. You sit there and think about how many thousands of people have leaned on this same rail across eighty years, celebrated and mourned and closed deals and marriages right here. Nothing about the place puts on airs, and still there is an order to the whole thing, a sequence, a way it is done. We ordered the works, the steak and the salad, family-style by tradition, and split the cut between us. My God. One of the best steaks of my life, and I live in Houston, for Chrissake, a city that takes its beef personally. I will admit I eyed the salad a beat too long, saying a small private prayer that Taylor Farms was nowhere near their romaine, but the whole table was almost too good to be true.

Then to bed early, because the flight back to Houston was an early one, back to the humidity and the dog and the pool and the home that, by the last night, we were both quietly ready for. Sometimes exploring is about the new thing, the city you have never seen, the steak you will talk about for a year. And sometimes it is just the long way of remembering what you already have. At the end of any good trip, it is always good to come home.