Pippin's Tavern

It was the night before the night before—well, several nights before—Christmas, and my friend Jenny and I had decided to venture out for one last holiday cocktail before the family madness set in.

I had The Peninsula Bar on the brain. I’d written about their hot toddy a few posts ago, and when I sat in on Alex & Amy’s Sunday afternoon radio show on WGN earlier this week, Amy couldn’t get over the place. “One of my favorite bars in the city is The Peninsula Bar,” she said early in the segment. I agreed. And later: “You know, there’s a really great fireplace at The Peninsula Bar.” True, too. This time of year, there’s also a very festive wreath hanging over those flames; the entire hotel, in fact, is decked out in such glittering cheer that no Scrooge stands a chance there.

Into two armchairs at a corner table we settled, thwarted in our quest to snag prime fireplace frontage due to a group who had staked out the spot early in the afternoon and, at 6 p.m., showed no indication of leaving. Who could blame them?

James, the bar manager, took our coats and suggested a couple of appropriately wintery options from the cocktail list. I ordered the Baja Slice: a warm mix of cinnamon-infused Patrón Reposado, RI1 rye, agave, and apple cider ($12); Jenny went for the L’Amour: Snow Queen vodka, limoncello, Canton (a ginger-flavored liqueur), egg whites, and raspberries ($15).

“Spotted: one ugly Christmas sweater,” Jenny said, tilting her head in the direction of a touristy gathering to our right. “It is festooned with color blocks and stripes.”

“Yes, but otherwise wouldn’t you say the crowd is pretty after-work stylish?” I asked.

“Mmm hmm,” Jenny agreed. “I’m seeing a majority of young, attractive urban professionals.”

Our efforts to celeb spot at this bar where celeb spotting is often reported were not successful—the lighting is too low to make out many faces, and James, the picture of professionalism, politely refused to comment—so we talked about celebrities instead.

Jenny: “Well, I read the Portia de Rossi eating-disorder book.”

The Chaser: “Unbearable Lightness? I saw her talking about it on Ellen just this afternoon.”

Jenny: “Oh! How were they together?”

TC: “They held hands and said they’ve changed each other’s lives. Portia said, ‘I’m not perfect; no one is,’ and Ellen said, ‘You’re perfect to me.’ Tears were shed.”

Jenny: “That’s sweet. She did get down to 82 pounds.”

The interior of The Peninsula Bar
The fireplace at The Peninsula Bar

That last part we shouted, since we were competing with the excited voices of some holiday revelers in a circular semi-private area behind our table (James did admit this is where celebrities are often seated, since it can be cordoned off). One woman in particular was having a really excellent time.

Jenny: “People are way drunker here than I expected at this time of day!”

TC: “Tis the season.”

Jenny: “I need a moment to wonder: Who would laugh like that?”

TC: “That type of sound would never emit from my body. I don’t bellow. I wheeze.”

We ordered a Volcano sushi roll ($28) at the recommendation of James, who proclaimed the warm lobster concoction his favorite menu item since the hotel’s opening, some ten years ago. When it came, our eyes widened. “This goes beyond pub grub,” Jenny said, in awe.

I had in mind that maybe we would make our way down Michigan Avenue, stopping in the lounges at the Four Seasons, the Ritz, and the Drake in a kind of battle-of-the-holiday-décor bar hop. Instead, we gathered our things and traipsed down the block to Pippin’s Tavern a bona-fide Mag Mile dive that we hear is popular with Peninsula staffers after hours. At Pippin’s, the seasonal trimmings consist of strands of white lights, poinsettias in the windows, and the bar’s usual urinal cake perfume. “Don’t worry. You’ll get used to it in a minute,” I told Jenny.

Our waitress took our drink order (I downgraded to a Bud Light on draft, price undetermined but cheap: Our bill for seemingly endless rounds, even after two other people, including the somewhat sloshed Creative Director, joined us, came to $63) and handed us menus from the hot dog place next door. “You can get pizza puffs with fries for $3.83!” Jenny whooped. We were experiencing a bit of culture shock.

We watched those poor horses pull their carriages past the window; we watched a man in a puffy vest select songs on the digital jukebox, an incongruous addition to this old-fashioned dive; and when the Enya song “Sail Away” came on, we declared ourselves in cozy holiday heaven. “I used to fall asleep to this song in high school,” Jenny sighed. “I used to take bubble baths to it in college,” I added.

Many songs later, we said our goodbyes on the snowy street outside. “Merry Christmas!” we yelled toward each other’s slamming cab doors. And to all a good night.