make-your-own-purse party at a condo on North Lake Shore Drive, my friends Jenny and Melissa, and I asked the building’s doorman for suggestions on nearby places to proceed with our evening.  

“Walk that way and take a left,” he said, pointing toward Irving Park Road. “Then go a couple more blocks until you see a big glittery sign…">
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Holiday Cheer, Thanksgiving’s Near; Plus, Black Wednesday Bashes

Last night, on our way out of a make-your-own-purse party at a condo on North Lake Shore Drive, my friends Jenny and Melissa, and I asked the building’s doorman for suggestions on nearby places to proceed with our evening.  

“Walk that way and take a left,” he said, pointing toward Irving Park Road. “Then go a couple more blocks until you see a big glittery sign…

Last night, on our way out of a make-your-own-purse party at a condo on North Lake Shore Drive, my friends Jenny and Melissa, and I asked the building’s doorman for suggestions on nearby places to proceed with our evening.  

“Walk that way and take a left,” he said, pointing toward Irving Park Road. “Then go a couple more blocks until you see a big glittery sign.”

“Woooo! A glittery sign!” we cooed, setting off as if en route to the Emerald City. It soon dawned on us that we were heading to Uptown’s Rat Pack–themed Holiday Club, an institution I’d visited only once before, for a birthday party two years ago. When we stepped inside the door at 9 p.m. and surveyed the main room, we spotted only a few groups playing pool and devouring the $5 meatloaf and mashed potatoes special. We ordered the same and chatted up two guys at the next table over: Rory, a cool young Londoner who just moved to Chicago on Monday, and Antoine, a native Parisian in his late 20s. Both work for an electronic cigarette company. “You get your nicotine fix, but without the 400 other chemicals,” they explained in dueling charming accents. “The smoke is actually water vapor.”

Over $3 Coors Lights, I tried to tell Rory what he was in for, come January: “When you wake up, it’s going to be 3 degrees out. The windchill will be negative 10.”

“I don’t really do Fahrenheit,” he said, “but I don’t think I’ve ever been that cold.”

At 10 p.m. we relocated to the karaoke room, where the bartender, Toots, was busily distributing enough alcohol to woo people up to the mic. First up: Tim, a part-time DJ from Niles doing a soulful rendition of “Hey Jude.” It was a decent start, and as he made his way back to his table, I asked him how, out of all the karaoke joints in all the neighborhoods in all Chicago, he had happened upon Holiday Club. “I Googled ‘karaoke in Chicago,’” he explained. Fair enough. As the room continued to fill up, we heard a wailing “Piece of My Heart,” sung by Whitney; a Mötley Crüe interlude from Toots; and an emotional rendition of “Defying Gravity,” from the musical Wicked, belted out by Amber and Valentine, whose other hobby is burlesque. My own pal Melissa spent the better part of two hours flipping through the songbook in search of our perfect duet, and though I was tempted by The Ting Tings’ “Shut Up and Let Me Go,” I somehow never got around to sing-shouting it to a crowd of 50 strangers.

On a final trip to the bar, I happened into a chat about Thanksgiving—fitting conversation fodder, I’d say, for the Holiday Club—with a fellow nonsinger, Josh, who celebrates every year with his family in rural Illinois. “What’s your signature dish?” I asked. “You know, your contribution to the meal?”

“Well, I’m usually responsible for the rolls, but this year I’m bringing salsa,” Josh replied.

“Salsa? Does that go with sweet potato casserole?” I wondered.

“It’s really good salsa,” he countered. “Who says no to salsa?”

My mother would definitely say no to Thanksgiving salsa, just as she always says no to my siblings and me partying it up the night before the holiday—aka the nightlife phenomenon bar owners love to promote as “Black Wednesday.” “The last thing I need is a bunch of overgrown layabouts sleeping it off in my house while I’m trying to get a 20-pound bird in the oven,” she huffs annually.

For those, however, who are allowed to let loose on November 25th (and aren’t holed up in who-knows-where, Wisconsin), here are three bars where the preholiday booze will be flowing:

Martini Park serves up $6 Absolut cocktails and live karaoke with the cover band Rendition from 8 p.m. to 2 a.m.

Landmark Grill & Lounge hosts Shout Out! What You Are Thankful For, a T-shirt-line launch party, with guest host Colin Egglesfield of the CW’s Melrose Place. The night includes $7 cocktails and chair massages.

Kit Kat Lounge & Supper Club celebrates the eve of Tina Turner’s 70th birthday with performances by the impersonator Traci Ross, half-price cocktails, and Thanksgiving-themed martinis ($12.50).

The Chaser will be off next week, recovering from a Kentucky Thanksgiving dinner; check back Thursday, December 3rd for more of Amalie’s exploits.

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