Your Guide to Family and Friends Night!

Wrigleyville is starting to look like a magical wonderland, with bars already decked out for the season eager to spread the holiday spirit.

We invite you all to our kickoff of the Wrigleyville Wonderland Happening December 9th from 5-8pm!

Celebrating the LARGEST pop up in the city of Chicago, we have 19+ bars and restaurants ready to help get you in the holiday spirit!

Enjoy drink specials, ice sculptors, photo opportunities, costume characters, giveaways, free samples of Kilwins hot cocoa and sing your heart out to your favorite Christmas carols with dueling pianos at Sluggers at 7pm! We top that off with an after party at Trader Todds where we will enjoy complimentary appetizers

Bring the kids as we have Santa making a stop on the rooftop of Old Crow and Mrs. Claus making a stop from the north pole to pick up the handwritten Christmas letters from the kids at Rizzo’s Lot.

We look forward to having you!

Schedule of Events

5:00: Guest arrives for check in at Moe’s Cantina: Tacos served for first 200 that check in 

5:15pm: Christmas letters W/ Mrs. Clause opens at Rizzo’s Lot

5:15pm: Santa makes stop at Santa’s Workshop on Old Crow’s rooftop

5:30pm: Ice sculptor begins demonstration outside of Rizzo’s lot.

6:00pm: Kilwins begins serving hot cocoa at store. (Cocoa served for the first 300 people that arrive to their store)

6:30pm: Amanda and her amazing band begins performance at Old Crow

7:00pm: Dueling Pianos starts at Sluggers (ONE free beer to first 100 people to stop in)

9-10pm: After party at Trader Todds W/ Free Appetizers

Friends and Family Night Exclusives

Moe’s Cantina – Whooville

3518 N. Clark Street

Moe’s becomes the celebrated holiday town of Whooville while offering a menu of shareable small plates, traditional full-size entrees, signature tacos and a cocktail list featuring house-made sangria, handmade margaritas, premium tequilas, and more. The first 200 people to check in will get free tacos!

Rizzo’s Bar and Inn – John Vincent’s Holiday Sing Along

3658 N. Clark Street

Local singing legend, John Vincent, will be performing some of the holiday hits from all of your old time lounge singer favorites like Frank Sinatra, Dean Martin and Louis Armstrong! From 5:15pm, join Rizzo’s to write Christmas letters with Mrs. Clause herself!

Old Crow Smokehouse – Santa’s Workshop

3506 N. Clark Street

Wrigleyville’s award-winning barbecue from the kitchen of pitmaster and “MasterChef” Tony Scruggs is the home of Santa’s Workshop. Decorated with oversized toys and ornaments and a larger than life Christmas tree, this is one you won’t want to miss with live music starting at 6:30! Then, head on up to their rooftop for our guest of the night… Santa!!

Wrigleyville Kilwins – 25 days of Chocolate

3519 N. Clark Street
Kilwins will offer caramel apples, hot chocolate and handmade chocolates perfect for gift giving for family, friends or yourself! Tonight, starting at 6PM Kilwins will be serving free hot cocoa the first 300 people in the doors of their pop up!

Sluggers Dueling Pianos

3540 N Clark St

Ready to sing your heart out? Join us at 7:00PM for holiday singalongs with Dueling Pianos! The first 100 people will get a free beer on us! Sing along to all your holiday favorites to finish off the night!

Trader Todd’s

3216 N. Sheffield Ave

Not ready to end the night after dueling pianos? We’re going to keep the party going at Trader Todd’s with free lite bites.

Stretch Bar & Grill – Elf’d Up

3845 N. Clark Street
Back by popular demand for a third year, it’s a full-blown tribute to the beloved Christmas movie “Elf,” Elf’d Up is a high-energy holiday pop-up bar, perfect for patrons who share Elf’d Up’s affinity for elf culture. They’ll have a $5 naughty or nice build your own hot chocolate bar!

Underground Lounge – Island of Misfits Toys

952 W. Newport Ave
Underground Lounge welcomes you to the “Pabst Island of Misfit Toys,“ to come hang out with Bumbles, Dolly, Hermey and others. The entire holiday drink menu will be 25% off! (21+)

NOLA Bar & Kitchen – A Very Cajun Christmas

3481 N. Clark Street
Inspired by the legend of Papa Noel, it’s a Cajun Christmas Story. In a deep swampy bayou of Louisiana, Papa Noel rides the river in a boat that’s pulled by alligators to send out presents. A very cajun Christmas offers unique New Orleans style Christmas decoration with classic cajun eats. It’s a place to gather friends and families and let the good times roll. Laissez les bons temps rouler with $5 Ho-ho Hurricanes, $5 Santa Sangria’s, and $3 Domestic cans until 7pm!

Winter at Gallagher Way

3635 N. Clark Street
Tonight only, enjoy half off Skate Rental if you have a 60613 Area Code!

Families, visitors and neighbors can celebrate the holidays by taking part in the many seasonal programs and activities at Gallagher’s Way Winterland return. This year includes the return of the famous Christkindlmarket Wrigleyville, ice skating on an 8,000-square-foot ice rink, curling and skating lessons, Santa’s Workshop, wreath making classes, holiday movie screenings, special programming at Hotel Zachary and much more.

Houndstooth Saloon – Griswolds

3369 N. Clark Street
Inspired by the famous family and the hilarious movies, Houndstooth Saloon has menu selections including “Yakkin on a bone,” a two-lb turkey leg, “Cousin Eddie’s” spiked eggnog and Clark’s Cocoa.
Special include free hot chocolate from 6-9pm!

All Our Festive Bars

The Country Club – Christmas Club

3462 N. Clark Street

Wrigleyville’s original Christmas pop up bar is back. Enjoy a classic Christmas party experience with themed food, drink, music and decor.

Diver at the Park – Santa’s Beach House

3475 N. Clark Street

Santa’s Beach House is here for its first Holiday season. Join Diver at the Park in their Tulum holiday inspired heated tent with their life sized palm trees decorated for a holiday on the beach. Get your Tulum holiday experience and cocktails in the heart of Wrigleyville.

Mordecai – Mistletoe

3632 N. Clark Street

Mistletoe, Mordecai’s annual holiday pop-up bar, boasts naughty and nice decorations and an exclusive holiday-inspired drink menu, featuring both contemporary and vintage cocktails.

Roadhouse 66 Gas N’ Grill – Jingle Junkie

3478 N. Clark Street

Serving up holiday inspired bites and sips in an explosion of cheer, Jingle Junkie and its heated, ski lodge inspired patio is the most festive spot to celebrate your upcoming holiday season. With an extensive seasonal cocktail /beer list and delicious festive bites that are sure to get even the grinchiest Grinch into the holiday spirit.

Deuces – Santa Baby Christmas Bar

3505 N. Clark Street

You better watch out! Santa Baby Christmas Bar is back offering a multi-room, multi-level, over the top Christmas experience

Vines on Clark- Apres Ski

3554 N. Clark Street

Fire pits available to rent! Enjoy cozying up by the fire with some of your favorite winter drinks!

The Graystone Tavern – 8 Crazy Nights – A Hanukkah Bar

3441 N. Sheffield Ave.

Back by popular demand for its third year, Chicago’s first and only Hanukkah-themed pop-up bar with decorations created for the Jewish holiday throughout the bar and weatherproofed beer garden, including over 14,000 blue and white lights and Hanukkah ball lanterns adorning the ceiling, Star of David and dreidel ornaments, lighted menorah decor, Mensch on a Bench, a Hanukkah sweater wall, an 8-foot inflatable dreidel and more.

HVAC Pub – The Christmas Pop UP

3530 N. Clark Street

HVAC will be transformed into a winter wonderland featuring Christmas drinks, food and music. Stop by for some awesome jams, incredibly festive ambiance, and seasonally special drinks!

Lucky Dorr – Lucky Lodge

1101 W. Waveland

Lucky Dorr, Chicago’s favorite craft beer destination, will transform into Lucky Lodge. A festive Winterland destination with special décor, the aroma of hot apple cider and rustic comfort galore.

Casey Moran’s – Rudolph’s Christmas Bar

3660 N. Clark Street

From the creators of Santa Baby Christmas Bar with all the Christmas spirits you know and love at Santa Baby with all new interactive social experiences and an incredible decor.