Chicago area holiday pop-up events 2023: Christmas themed bars, ugly sweater parties and more
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CHICAGO (WLS) — The holiday season is in full swing and pop-up events around Chicago are ready to celebrate ‘the most wonderful time of the year.’

Whether you think you are on the nice or naughty list, you can check out Santa, take a picture with the Grinch, and lay back sipping on festive drinks across these seasonal pop-ups.

How The Grinch Stole Christmas At Moe’ Cantina

Moe’s Cantina is all decked out for the holidays.

The Grinch stole Christmas and brought it to Moe’s Cantina?

That’s right you can catch the Grinch and rock your ugly sweater while enjoying authentic Mexican cuisine at this Christmas pop-up. Who said festive cocktails and a picture with the Grinch isn’t the best way to end this year?

Address: 3518 N. Clark

Hours: Mon: Closed | Tuesday – Thursday: 5:00 p.m. – close | Friday: 2:00 p.m. – 2:00 a.m. | Saturday: 11:00 a.m. – 3:00 a.m. | Sunday: 11:00 a.m. – 7:00 p.m.

Ugly Sweater Party At Nola Bar & Kitchen

Ugly Sweater bar is the place to rock your festive sweater this season.

Looking for an excuse to flex that ugly Christmas sweater you have stored in your closet?

NOLA has become an Ugly Sweater Bar, and they encourage you to embrace all the tackiness! Join them every Friday night for karaoke and sing the night away with Christmas tunes.

Address: 3481 N. Clark

Hours: Mon – Thurs, 12:00 p.m. | Fri 12:00 p.m. – 3:00 p.m. | Sat 12:00 p.m. | Sun 12:00 p.m. – 10:00 p.m.

ALSO SEE: Naperville family celebrates ‘Swiftmas’ with Taylor Swift-inspired decorations

Pawlidays at River Shannon:

Established in 1946 and located at the heart of Lincoln Park, dog-friendly neighborhood favorite River Shannon is celebrating the season with over-the-top holiday decor, festive drinks, holiday beers on tap, and, of course, holiday-themed treats for all furry visitors.

From the holiday menu, to holiday board game nights, the River Shannon is the place to celebrate the holiday with your dog.

Upcoming holiday-themed events:

Dog Photos with Santa: Santa Claus is coming to River Shannon! Patrons can stop in with their furry friend on Sunday, Dec. 3rd from 12 3 p.m. for a complimentary photo op with Santa.

Holiday Cookie Turn-Up Service: Every Monday night in December at 9 p.m., River Shannon will be spreading extra joy to valued patrons with a special complimentary cookie delivery during the Holiday Cookie Turn-Up Service.

Guests can cozy up at the pub, savoring delicious holiday-themed cocktails, while being served up warm, freshly baked cookies right to their tables.

Address: 425 W. Armitage Ave

Hours: Mon-Fri, 12 p.m. – 2 a.m. | Sat, 11 a.m. – 3 a.m. | Sun, 11 a.m. – 2 a.m.

Holiday Lodge at The Lodge Tavern:

Division Street’s favorite bar is getting a holiday makeover complete with a full month of holiday events!

The Lodge Tavern-already known for its cozy winter cabin feel- is transforming into a holiday wonderland complete with twinkling lights, wreaths, garland, and more.

From the holiday menu, guests can choose from festive riffs on classic cocktails like Mule-Tide Greetings, Ebenezer’s Old Fashioned, Mrs. Clausmo, holiday beers on tap, and more.

For those looking to warm up from these chilly temperatures, the Lodge Tavern will offer a hot cocktail menu featuring the Ho Ho Hot Toddy, Irish You A Merry Christmas, St. Nicks Cider, and more.

Upcoming holiday events at The Lodge:

Letters from The Lodge: This holiday season, The Lodge is spreading joy and sending warm wishes to heroes stationed overseas. Gather with friends and family while sipping on holiday beverages and compose heartfelt messages of gratitude to service men and women stationed overseas on custom Lodge holiday postcards.

Cookie Decorating: Kick off the week every Monday in Dec. from 3 p.m. to 5 p.m. with a festive and fun-filled evening of complimentary cookie decorating at The Lodge. Sip on seasonal beverages while creating edible masterpieces with icing and festive toppings.

Dog Photos with Santa: Santa Claus is coming to The Lodge Tavern! You can stop in with your furry friend on Sunday, Dec. 3rd from 12 p.m. to 3 p.m. for a complimentary photo opp with Santa.

Address: 21 W. Division St

Hours: Sun-Fri, 10 a.m.- 4 a.m. and Sat, 10 a.m. – 5 a.m.

Holiday Singalong at The Redhead Piano Bar:

Sing along to your favorite Christmas carols at Redhead Piano Bar! The Redhead Piano Bar invites you to sing along to all the holiday classics with nightly live piano music and performances from 7 p.m. to 4 a.m. The cozy late night spot decked out with festive lights, and mistletoes will feature a special limited time holiday cocktail menu.

Address: 16 W. Ontario St

Hours: Sun-Fri, 7 p.m. – 4 a.m. and Sat, 7 p.m. – 5 a.m.

Holiday Dueling Pianos at The Original Mother’s

The Original Mother’s is getting into the holiday spirit with weekly dueling piano theme parties every Saturday in Dec. from 9 p.m. to 12 a.m.! Guests are invited to dress up, bring their favorite song requests, and revel in live holiday sing-along piano shows consisting of two grand pianos and charismatic entertainers behind the keys with the addition of a rock band drummer.

Upcoming holiday dueling piano parties include:

Sat, Dec 2: Ho Ho Ho-down

Sat, Dec 9: Classic Christmas Characters

Sat, Dec 16: Ugly Sweater Party

Sat, Dec 23: Naughty or Nice

Sat, Dec 30: Christmas Pajama Party

Address: 26 W. Division St

Hours: Thursday & Friday: 7 p.m. – 4 a.m. | Saturday: 7 p.m. – 5 a.m.

Winterland at Gallagher Way

Gallagher Way Chicago is ready for the holidays as it transformed into a winter wonderland!

Stop by at Gallagher Way for nonstop fun in a winter wonderland!

This year’s expanded programming will offer guests more family-friendly activities and new interactive experiences, along with returning favorites, including Christkindlmarket Wrigleyville and the Gallagher Ice Rink, with the rink now located inside the iconic ballpark.

Rides include a winter tube, Infield Express, Hot Cocoa Cups, and Winter Whirl. There will also be fun carnival games with a winter twist, like Chimney Toss, Tree Topper, and Snow Pitch. Stop by for nonstop winter fun!

Address: 3635 N. Clark

Running from Nov. 21, 2023, through Sunday, Jan. 7, 2024

Christmas Club At Country Club

It’s the holidays so that means Country Club transforms into Christmas Club! Enjoy a two-story classic Christmas party experience with three rooms and three bars! Stick around long enough and you may see our friend from the North Pole and his helpers make an appearance.

Address: 3462 N Clark

Hours: Monday – Thursday – 4 p.m. – 2 a.m. | Friday – 1 p.m.- 2 a.m. | Saturday 11 a.m. – 3 a.m. | Sunday 11 a.m. – 2 a.m.

8 Crazy Nights At Graystone Tavern

Chicago’s first and only Hanukkah-themed pop-up bar has returned! Graystone Tavern has transformed into a Hanukkah Haven. You will find blue and white decorations covering the bar from top to bottom and an entire wall of Hanukkah sweaters that adds that festive touch. Sip Hanukkah-inspired cocktails in their weatherproofed beer garden, which is covered in over 30,000 blue and white lights, Hanukkah ball lanterns, Star of David and dreidel ornaments, Mensch on a Bench, an 8-foot inflatable dreidel and more!

Address: 3441 N. Sheffield

Open from November 25th – January 9th

Jingle Junkie At Roadhouse 66

Calling all the jingle ladies! You will not be able to recognize Roadhouse 66 during the holiday season. This ski lodge inspired pop-up will make you feel ready to hit the slopes. Cozy up with a hot cocktail by the fireplace, and pair it with some of delicious comfort food! Ski lodge, cozy food, warm drinks? Sounds like a complete Christmas vibe you don’t want to miss out.

Address: 3478 N. Clark

Hours: Mon: 3 p.m. – 2 a.m. | Tue: 3 p.m. – 2 a.m. | Wed: 3 p.m. – 2 a.m. | Thu: 3 p.m. – 2 a.m. | Fri: 12 p.m. – 2 a.m. | Sat: 11 a.m. – 3 a.m. | Sun: 11 a.m. – 2 a.m.

Santa Baby At Bamboo Club

For the Holiday season, jaw dropping Santa Baby Christmas bar will make you spill your milk and cookies.

Bamboo Club is usually an island inspired getaway, where patrons go to sip from pineapples and dip their feet in the pool. For the Holiday season, this jaw dropping Christmas pop-up will make you spill your milk and cookies. Have the chance to be on the nice list by enjoying fishbowl-style cocktails, and festive bites. Make sure you come with your phone fully charged, as every inch of this double-decker bar is Insta-worthy for selfies.

Address: 3505 N. Clark St

Hours: Monday – Thursday: 11 a.m. – 11 p.m. | Friday: 11 a.m. – 2 a.m. | Saturday: 9 a.m. – 3 a.m. | Sunday: 9 a.m. – 11 p.m.

Elf’d Up At Stretch Chicago

Inspired by the Christmas Classic Elf (2003) Stretch Chicago looks like a Hollywood movie set. Elf décor hangs from the ceiling, elf mugs are available to sip out of, and cardboard cutouts from the movie are all around to take photos with! Buddy’s breakfast pasta is on the menu, you know, spaghetti with mini marshmallows, M&Ms, rainbow sprinkles, and garnished with chocolate syrup? It’s also been rumored that Buddy the Elf hangs around and can often be found smiling, don’t forget to snap a picture!

Address: 3845 N. Clark

Hours: Monday – Thursday 3 p.m. – 2 a.m. | Friday 11am to 2 a.m. | Saturday 10:30 a.m. to 3 a.m. | Sunday 10:30 a.m. to 2 a.m.

Mordecai Mistletoe At Mordecai

Mordecai’s pop-up bar, Mistletoe, is the romantic winter spot you can’t miss.

“I should be playing in the winter snow, but imma be drinking at Mistletoe.” Mordecai’s popup bar, Mistletoe, is an elegant romantic winter spot. Sip on exclusive holiday-inspired drinks featuring both contemporary and vintage cocktails. Food and cocktails under the Mistletoe? You can’t beat that. Reservations can be made now!

Address: 3632 N. Clark Street

Hours: Sunday – Thursday 5:00 PM – 10:00 PM | Friday – Saturday 5:00 PM – 11:00 PM

Island of Misfit Toys at Underground Lounge

Wrigleyville’s best kept secret just flipped on the festive switch on and became the Island of Misfit Toys. Fans of the Christmas classic Rudolph the Red-nosed Reindeer should consider this pop-up a must see! Enjoy themed cocktails named after all your favorite characters and dance to underground musicians.

Address: 952 W. Newport

Hours: Monday – Friday 7 p.m. – 2 a.m. | Saturday 7 p.m. – 3 a.m. | Sunday 7 p.m. – 2 a.m.

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