Walking in a Wrigleyville Wonderland
The stockings are hung, the sleigh bells are ringing, and the drinks are pouring, Wrigleyville Wonderland is back! The baseball-centric neighborhood transforms into the North Pole with tons of Holiday themed bars. These pop-ups did much more than deck the halls, they’ve decorated every square inch of their spaces to bring holiday joy to even the grouchiest of grinches. Here is where you and your crew can come spread some cheer.
Join us for Friends and Family Night on Wednesday, December 7th, from 5 to 8 pm!
Enjoy free hot cocoa, complimentary treats at participating bars, snap photos with popular Christmas characters, and more! Meet at Moe’s Cantina to check in and get your wristband. All ages are welcome!
Click here to register!
Winterland at Gallagher Way
3635 N Clark
Running from Friday, November 18, 2022, through Sunday, January 8, 2023.
Get ready for Winterland at Gallagher Way! 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 wintertube, 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!
3462 N Clark
Opening November 16th.
In November and December, Country Club becomes Christmas Club! Enjoy a two-story classic Christmas party experience with three rooms and three bars! If you stick around long enough, you may catch a glimpse of Santa and his helpers sneaking in some Holiday fun.
8 Crazy Nights
3441 N Sheffield
Open from November 25th – January 9th.
Chicago’s first and only Hanukkah-themed pop-up bar has returned! Graystone Tavern has transformed into a Hanukkah Haven. Blue and white decorations cover the bar from floor to ceiling, and the wall of Hanukkah sweaters adds the perfect amount of pizzaz. Sip Hanukkah-inspired cocktails in their weatherproofed beer garden, which is covered in over 14,000 blue and white lights, Hanukkah ball lanterns, Star of David and dreidel ornaments, Mensch on a Bench, an 8-foot inflatable dreidel and more! Warm up with traditional and spins on Jewish favorites like Matzo Ball Soup and Latkes. Board and card games will be available to guests nightly, including Connect 4 with Hanukkah gelt, Cards Against Humanity Jew expansion pack, Mitzvah Match, Jewish Guess Who, Dreidel, Apples to Apples Jewish edition, and Schmear Build-A-Bagel card game.
3478 N Clark
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!
3505 N Clark
Deuce’s MLB Bar is famous for their over the top decorations. For the Holiday season, this jaw dropping Christmas pop-up will make you spill your milk and cookies. Dare we say the decor of Santa Baby is best in snow? Make your way to the nice list by sharing one of their fishbowl-style cocktails, and don’t skip out on festive bites. Make sure you come with your phone fully charged, for every inch of this double-decker bar is insta-worthy for elfies.
3845 N Clark
Opens November 11th.
Treat every day like Christmas! Inspired by the Christmas Classic Elf (2003) Stretch Chicago looks like a Hollywood movie set. Elf decor 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 has all four major food groups! It’s also been rumored that Buddy the Elf hangs around and can often be found smiling, it’s his favorite!
3632 N Clark
Opens November 18th.
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. Reservations can be made now!
Island of Misfit Toys
952 W Newport
The Island of Misfit Toys allows us to imagine that maybe our flaws are actually just uniqueness misunderstood. Your favorite basement club, Underground Lounge, has become the Island of Misfit Toys! Fans of the Christmas classic Rudolph the Rednose Reindeer should consider this pop-up a must see! Enjoy themed cocktails named after all your favorite characters and dance to underground musicians. Everyone fits in at the Island of Misfit Toys.
Lucky Dorr has brews for all and all a good night! This Holiday season, warm up with festive Christmas-inspired ales you can find nowhere else. Located steps away from Gallagher Way, you can warm up from your Holiday activities without having to drive your sleigh too far. Dogs are ALWAYS welcome at the Lucky Lodge, it’s pawsitively a great time!
Grinch Stole Christmas
3518 N Clark
Opens November 18th
No one should be alone on Christmas, or even the whole holiday season! The Grinch stole Christmas, and left it at Moe’s Cantina! Chow down on some authentic Mexican cuisine while being lost in this Christmas wonderland. Stick around long enough and you’ll see the Grinch himself! Don’t be afraid to ask for a photo, after a few margaritas he is more friendly than Whoville gives him credit for.
Ugly Sweater Bar
3481 N Clark
Open from November 15th to January 15th.
Looking for an excuse to flaunt that ugly Christmas sweater you spent more on than you’d like to admit? NOLA has become the Ugly Sweater Bar, and they encourage you to embrace all the tackiness! This Clark Street bar celebrates Mardi Gras year round, but for the holidays they are doubling down with being Christmas obsessed as well. Join them EVERY Friday night for karaoke! Grab the mic, hop on stage, and put that ugly sweater under the spotlight.
3636 N Clark
Opening November 18th.
Grab your fleece and flannel, and head over to the Lumberjack Lodge to relax and cozy up! Smoke Daddy has turned this BBQ, blues, and beer joint into a Lumberjack’s dream getaway. Be greeted by a larger-than-life bear wearing a checkered scarf, enjoy dimmed lighting by lanterns that are placed as centerpieces on every table, and rows of Christmas trees to get lost in. You’ll feel like a true lumberjack, without being out in the freezing cold! Join them for their grand opening party on Friday, November 18th for holiday cocktail specials and a wood carving demonstration from 6 pm to 8 pm. They also have a HUGE list of Holiday activities you do not want to miss, like brunch with Santa, a boozy gingerbread house party, and more!
Reserve your spot for any of their winter activities here.
Rock and Roll Christmas
3530 N Clark
Known for great pizza and live music, HVAC Pub is the go-to destination for live music year-round in Wrigleyville. Step out of the cold and into the rock haven of HVAC. Sometimes, Christmas music doesn’t cut it. HVAC has live DJs, rock bands, and more all winter long! Check their website for a full music schedule.
Old Crow Smokehouse
Santa’s elves we’re hard at work this year at Santa’s Workshop. They couldn’t make Christmas magic come true in a space that wasn’t as festive as they are! They converted Old Crow Smokehouse into a holly jolly Christmas toy house. Admire the towering nutcrackers and the rocking chair horse that is larger than life! Make your own Christmas magic happen with a little help from a themed cocktail, like the Jack Frost or the Raspberry Waffle.