Over-the-Top Holiday Pop-Ups to Grab a Festive Drink

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We get it, Chicago! The cold is bitter and it’s oh-so-tempting to have your glass of wine at home by the fire. But the holiday season—with light displays, ice skating rinks scattered around town, fancy teas and more holiday shows than you can possibly see— is an absolutely magical time in our city. We’re sharing our favorite holiday pop-up bars (some that even welcome kids!) that will make venturing outside totally worth it.

Lakeview Chamber of Commerce

8 Crazy Nights

Don’t miss the first-ever Hanukkah pop-up in all of Chicago! This no-cover pop-up at The Graystone Tavern includes Hanukkah-inspired decor, themed food, drinks, and Schmaltz beers on tap. To get everyone in the proper spirit, Classic Eastern European Jewish dishes will be served, such as matzo ball soup, latkes, jelly donuts and brisket.

Dec. 1 – 31; The Graystone Tavern, 3441 N. Sheffield. More info.

Jill Wellington via Pixabay

Bad Santa Photo Shoot

He’s making his list, he’s checking it twice. . . and he doesn’t care if you’re naughty or nice. Bad Santa is coming to town! For one night only, have your photo snapped with Bad Santa at Sheffield’s.

Dec. 7, 6 p.m.-10 p.m.; Sheffield’s, 3258 N. Sheffield. More info


Lakeview Chamber of Commerce

Christmas Club

This no-cover pop up spanning three different rooms in three different bars includes guest DJs every week and appearances by Santa, as well as other various Christmas characters.

Nov. 20-Jan. 1; Country Club, 3462 N. Clark. More info.

Lakeview Chamber of Commerce

Elf’d Up

Rejoice! Your favorite Buddy the Elf themed bar is back! Enjoy “Elf” specialty cocktails, rotating seasonal drafts and themed food, including Buddy’s famouns breakfast pasta. Expect weekly Buddy the Elf appearances every Thurs.-Sat. (anytime between 9 p.m.-midnight). Gather your friends for Elf Movie Trivia, Dec. 4, 11 & 18 at 7 p.m. and brunch every Sat. and Sun., 11 a.m.-2 p.m.

Nov. 20-Jan. 21; Stretch, 3485 N. Clark. More info

Lakeview Chamber of Commerce

Griswold’s Christmas Vacation

Throw on your favorite Cousin Eddie-inspired dickie and head to Wrigleyville’s favorite bar for college football and good ole’ country. They’ll have Griswold- and 80s-themed food, drinks, and specials, the bar will feature Cousin Eddie’s decked out 1977 RV, three themed rooms, The Griswold living room, the tiki Bar, and Clark’s attic. A $5 cover goes into effect after 5 p.m., or you may donate a toy to Toys for Tots in lieu of the cover fee. There will be a champagne toast at midnight each night.

Nov. 17-Feb. 9; Houndstooth Saloon, 3369 N. Clark. More info


Lakeview Chamber of Commerce

Jingle Junkie

This newbie to the Christmas pop-up scene is coming in HOT (or should we say cold? Jingle Junkie will have a heated ski lodge-inspired patio with rotating holiday seasonal beer and cocktail list along with festive food to pair. 

Nov. 27-Jan. 6; Roadhouse 66, 3478 N. Clark. More info.

Frans Van Heerden via Pexels

John Vincent Pop-Up Shows

Chicagoans know John Vincent as a local legendary performer, entertaining crowds of all types and varieties with his covers of Frank Sinatra, Louis B. Armstrong, Johnny Cash and more. He is also the current resident National Anthem singer for the Chicago Cubs. The December 12 pop-up will be a special Sinatra birthday performance!

Dec. 5, 6, 12, 15, 19, 20, 21 & 22; Rizzo’s Bar & Inn/365-viii, 3658 N. Clark. More info

Lakeview Chamber of Commerce

Mistletoe Holiday Pop-Up

The second-floor cocktail restaurant of award-winning Mordecai is bursting at the seams with holiday spirit and mistletoe! Enjoy the festive over-the-top decor and a specialty holiday cocktail menu.

Nov. 22-Jan. 1; Hush Money/Mordecai, 3632 N. Clark. More info

Lakeview Chamber of Commerce

Rock N Roll

Rotating holiday-themed drink and food specials, and musical performances are sure to have you rockin’…and not just around the Christmas tree! There is a cover fee, but you may substitute the fee with a toy donation. Be sure to wear your favorite ugly Christmas sweater because there will be a $100 prize for the ugliest. 

Dec. 21-Jan. 31; HVAC Pub, 3530 N. Clark. More info

Hotel Zachary

Glamping at Hotel Zachary

Through late February, Camp Zachary will pop-up on the terrace of Hotel Zachary. Overlooking the excitement of Winterland at Gallagher Way, visitors to Camp Zachary can relax on comfy couches and enjoy cozy festive décor with hot toddy’s and fire cauldrons to stay warm. Children aged 12 and under will receive complimentary hot chocolate and cookies Camp Zachary will be the Instagrammable moment not to be missed this winter and reservations are available for groups up to 10 people for two-hour windows. For the latest on reservations and availability, please visit Resy.com.  

Nov. 22-late Feb.; Hotel Zachary, 3630 N. Clark. More info.

Lakeview Chamber of Commerce

Rudolph’s Christmas Bar

Experience the true spirit of Christmas with one of everyone’s favorite Christmas red-nosed characters, Rudolph! There are multiple bars within Rudolph’s Christmas Bar: Grinch’s Piano Bar, Frosty’s Rooftop, Rudolph’s Lounge & more and character appearances include Rudolph, The Grinch, Frosty, Santa & more. They are also partnering with Toys for Tots and will have donation bins on-site for daily collection. 

Nov. 22-Jan. 6; Casey Moran’s, 3660 N. Clark. More info

Lakeview Chamber of Commerce

Santa Baby Christmas Bar

Deuce’s Major League Bar’s pop-up includes multiple bars, a Gingerbread Village, Alpine Ski Lounge, Santa’s Workshop, WInter Wonderland and more. They will be partnering with Toys for Tots and will have on-site bins for donations with daily collection. It’s recommended you purchase tickets in advance as door ticket price subject to change. Kids welcome prior to 8 p.m.

Nov. 20-Jan. 6, Deuce’s Major League Bar, 3505 N. Clark. More info


Santa’s Workshop

Celebrate a country-style Christmas at this all-ages, no-cover pop-up featuring special menus, massive holiday decor, and three floors of festivities. There will be several giant Christmas trees and Santas, as well as two enormous rocking chairs, perfect for a photo op. See Santa take off in his reindeer-led sleigh and roast marshmallows while Christmas movies play on the screens.

Month of Dec.; Old Crow Smokehouse, 3506 N. Clark. More info

Gallagher Way

Gallagher Way’s Winterland

Gallagher Way will be decked out with holiday flare bigger and brighter than ever before! Winterland includes the return of the famous Christkindlmarket, ice skating on an 8,000-square-foot ice rink, curling and skating lessons, Santa’s Workshop, wreath-making classes, oversized decorative winter characters, holiday movies and much more. This year’s transformation will include a 30-foot holiday tree underneath the Wrigley Field Marquee, a tree lot at Big Star Wrigleyville and more.

Nov. 22-Feb. 16; Gallagher Way, 3635 N. Clark. More info

— Maria Chambers


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