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  • Daily Email - Monday - 12/22/2025

Daily Email - Monday - 12/22/2025

New Year’s is creeping up, and winter isn’t slowing down. Good thing we’ve got heated patios, parties, and giveaways that go harder than your favorite holiday cookies. Let’s keep it going.

One lucky winner’s about to live the main character in a Chicago rom-com fantasy: we’re talking a luxury hotel stay, bougie meals, cocktails, and a skyline view that might make you tear up a little. Win the Downtown Chicago Getaway.

JUST ANNOUNCED

BEST HEATED & ENCLOSED PATIOS

Photo: ebkphoto.com

You don’t have to suffer to socialize this winter. Our guide to Chicago’s heated and enclosed patios is stacked with warm spots for drinking, dining, and pretending it’s not 14 degrees out.

MUSEUM OF BROADCAST COMMUNICATIONS PRESENTS

EXPLORE THE EVOLUTION OF LATE NIGHT TV

Chicago’s Museum of Broadcast Communications is back with a deep dive into late-night TV. See the legends, the weirdos, and all the moments that changed culture like never before. Buy tickets before it's gone!*

THIS MONTH

THRU 01.04 - ALL YOU CAN PUTT at PUTTSHACK - SKOKIE*

WED. - ONE LAST SLAY at THE PROMONTORY

FRI. - TRANS-SIBERIAN ORCHESTRA at ALLSTATE ARENA

12.31 - LEMOYNE ALEXANDER at REGGIES (win)*

THE LAST MINUTE GIFT THAT STILL WINS

Running out of time? Rosetta Stone’s Holiday Sale has your back. Get lifetime access to all 25 languages for $149, normally $399, with instant delivery. One tap and you have a gift that feels thoughtful and cool, not rushed. Perfect for anyone who loves going places and trying new things. The lessons are fun, the method works, and they will actually use it.*

NYE AT DAVE & BUSTER’S

Ring in 2026 surrounded by flashing lights, great food, and unlimited arcade play. Whether you’re rolling deep with the family or going 21+ after dark, plan ahead now.*

LOCALS ONLY

  • Sonic fans, your time has come. This Sonic The Hedgehog Pop-Up Cafe is serving favorites through February in Wicker Park. Gotta go fast!

  • Chicago’s biggest Jewish Christmas Eve party returns. It’s Matzo Bash on Wednesday at Joy Distrist. L’chaim!

  • Two very different winter drinking fests were just announced, both extremely valid: Cider Summit on January 31st and Tequila Tasting Fest on February 14th.

  • This is Halloween and Christmas. Free bingo is going down tomorrow night at Lizards Liquid Lounge. There will be music, prizes, and popcorn. Learn more.

WIN STUFF

🚨 LAST CHANCE:

🔥 TRENDING:

Time’s ticking on knocking everything off you Chicago Holiday Bucket List. Do it before it’s too late.