The Most Festive Holiday Pop-Ups in Chicago
via Smoke Daddy
Ho, ho, ho! The festive season is upon us and you know Chicago LOVES to show off for the holidays. There may be freezing temperatures and snowy streets, but the twinkling lights, opulent décor and holiday fun more than make up for it (for now at least!). Here are some holiday events and pop-ups to enjoy around the city in the coming weeks:
Smoke Daddy {3636 North Clark Street, Chicago, IL; 773.227.2583}
Smoke Daddy’s Winter Wonderland is heading to Wrigleyville for the season! The restaurant’s spacious interior will transform into a floor-to-ceiling holiday pop-up inspired by a nostalgic 1950s Christmas at home. Guests can expect tinsel-draped walls, glowing red-and-green décor, a wreath wall ornament installation, and cozy fireside sitting areas perfect for photos! Enjoy festive cocktails, weekly Wednesday Family Nights (with Christmas cookie decorating, letters to Santa, snowman making, etc.), Thursday Trivia Nights (Elf, Home Alone, A Christmas Story) and an epic Santa Brunch on Saturday, December 20.
Also, be sure to stop by Smoke Daddy’s Wicker Park location for a final farewell this month as it will shutter at the end of December.
via Park Hyatt
Park Hyatt Chicago {800 North Michigan Avenue, Chicago, IL; 312.335.1234}
A taste of decadence awaits with a trip to ‘Champagne Row’ at Park Hyatt Chicago. Rooted in Chicago’s legacy of print and publishing, Champagne Row is an experience that blends literary heritage with refined indulgence. Inspired by the historic Printer’s Row neighborhood, the transformed library invites guests to sip, savor, and celebrate the art of storytelling. Indulge in a rotating menu of exceptional Champagnes by the glass or bottle, perfectly paired with your choice of complimentary elevated bites, all while surrounded by shelves curated in collaboration with Open Books (a used bookstore located in West Loop)!
Offered Thurs-Sat from 3-8pm.
Three Dots & A Dash {435 North Clark Street, Chicago, IL; 312.610.4220}
Beloved tiki bar Three Dots & a Dash is getting a winter makeover with the arrival of their ‘River North Pole’ bar pop-up! Their space has been transformed from a tropical paradise into a snowy winter wonderland escape, complete with winter and holiday decorations throughout. Sip from Three Dots & a Dash’s exclusive holiday cocktail menu featuring both delicious hot cocktails and creative themed drinks all served in festive glassware, including a specialty Snowman mug for all holiday mug collectors! Their retail program is open in the bar daily providing a one-stop-shop for holiday gifting for all those cocktail connoisseurs in your life!
via The Hotel Zachary
Hotel Zachary {3630 North Clark Street, Chicago, IL; 773.302.2300}
Located in the heart of Wrigleyville and overlooking the Christkindlmarket, Hotel Zachary and its social bar and lounge, Alma, have transformed into a cozy winter retreat, complete with returning favorites like Breakfast with Santa, Teddy Bear Tea and Globes on the Terrace, as well as a brand new ‘Holiday Charcuterie Workshop’! Alma’s lively bar and lounge is aglow with holiday décor and a cheerful soundtrack, featuring a live DJ on select evenings, so guests can cozy up over spirited cocktails, festive bites, and good company all winter long!
Reservations are required for all holiday events.
Sheraton Grand Chicago Riverwalk {301 East North Water Street, Chicago, IL; 312.464.1000}
Ring in the holidays at the Sheraton Sleigh Bar, a limited-time holiday pop-up located inside the Sheraton Grand Chicago Riverwalk. Presented by Shula’s Steak House, this festive experience transforms Shula’s private dining room into a cozy winter retreat filled with twinkling lights, nostalgic décor, and sleigh-themed photo ops perfect for your holiday memories. Sip on signature holiday cocktails, feast on festive bites, take part in family-friendly holiday activities designed to delight guests of all ages and enjoy visits from Santa throughout December!
Admission is free but reservations are encouraged.
via The Dandy Crown
The Dandy Crown {694 North Milwaukee Avenue, Chicago, IL; 312.846.6420}
Make your holiday season extra *dandy* with a visit to Dandy Crown’s 4th annual holiday pop-up, ‘A Very Dandy Holiday'! This epic event celebrates the season with specially themed cocktails (both alcoholic and non-alcoholic) served in joyful, garnished stemware along with holiday cheer and décor throughout the interior and outdoor heated patio spaces. A Very Dandy Holiday is free to attend with walk-ins accepted, but reservations are still highly encouraged.
Available through January 4, 2026.
Graystone Tavern {3441 North Sheffield Avenue, Chicago, IL; 773.666.5450}
The original Hanukkah bar is back by popular demand for the third year in a row at Graystone Tavern! During their ‘8 Crazy Nights’ Hanukkah celebration, Graystone Tavern will be serving up delectable Jewish dishes and some pretty remarkable, Hanukkah-themed cocktails like Mazel Tov, Dreidel Bomba, and Hanukkah Harry’s Hot Chocolate. Expect all the customary blue and white lights and decorations throughout their indoor area as well as in the weather-proofed beer garden for those who wish to take the celebrations outdoors!
By Robyn Glaza | Market Manager