Wrigleyville is getting ready for another Christmas season filled with elaborate holiday pop-up bars, festive cocktails, Christkindlmarket at Gallagher Way and the return of TBOX. More than 20 holiday bar concepts have been announced for 2026, with seasonal celebrations beginning in early November and continuing into December and, at select venues, January.
From Santa Baby and Elf’d Up to Winterland outside Wrigley Field, here’s a guide to the Christmas bars, opening dates and major holiday events around Wrigleyville in 2026.
Wrigleyville’s 2026 Christmas and holiday pop-up bars
The Lakeview East Chamber of Commerce’s Wrigleyville Wonderland guide lists the following 22 themed bars and restaurants. A few opening dates are still to be announced.
| Bar or restaurant | 2026 Christmas theme | Scheduled opening |
|---|---|---|
| Underground Lounge | Island of Misfit Toys | November 1 |
| Stretch Chicago | Elf’d Up | November 7 |
| Brickhouse Tavern | Home Run Holidays | November 11 |
| Almost Home Tavern & Grill | Almost Home Alone | November 13 |
| Kincade’s Wrigley | Christmas at Kincade’s | November 13 |
| Roadhouse 66 | Jingle Junkie | November 13 |
| The Cubby Bear | The Polar Bear | November 16 |
| Sports Corner | Santa’s Scoreboard | November 16 |
| Country Club | Christmas Club | November 20 |
| Big Star Wrigleyville | Holly Dolly Honky Tonk | November 20 |
| Mordecai | Mistletoe at Mordecai | November 20 |
| Moe’s Cantina | Noche Buena | November 20 |
| Stolen Saddle | Santa Baby Bar | November 20 |
| Merkle’s | The Nutcracker | November 20 |
| The Graystone Tavern | 8 Crazy Nights | November 23 |
| Brokedown Palace | Brokedown Christmas | November 23 |
| Happy Camper | Happy Alchoholidays | November 23 |
| Billy Goat Tavern | Santa’s Reingoats | November 27 |
| Dad’s Place | Santa’s Place | December 1 |
| Rizzo’s | Candy Cane Lane | To be announced |
| Lucky Dorr | Lucky Lodge | To be announced |
| Old Crow Smokehouse | Santa’s Workshop | To be announced |
The holiday bars to know
Santa Baby Bar: One of Clark Street’s biggest holiday transformations returns with elaborate decorations, multiple themed areas, festive food and cocktails, and plenty of photo opportunities. The venue lists a season extending into early January. Santa Baby information and reservations.
Elf’d Up at Stretch: The Elf-inspired pop-up is scheduled to open November 7 at 3485 N. Clark Street, featuring a holiday movie theme, decorations and specialty offerings. Elf’d Up details.
Jingle Junkie at Roadhouse 66: Opening November 13 at 3478 N. Clark Street, with its winter holiday makeover and ski-lodge-inspired atmosphere. Jingle Junkie details.
Christmas Club at Country Club: Scheduled to open November 20 with festive décor and holiday drinks. Country Club information.
Noche Buena at Moe’s Cantina: Scheduled for November 20, bringing a Latin-inspired holiday theme to Wrigleyville. Noche Buena details. Other announced seasonal concepts include Holly Dolly Honky Tonk at Big Star, The Polar Bear at Cubby Bear, The Nutcracker at Merkle’s and Almost Home Alone at Almost Home.
Winterland and Christkindlmarket at Wrigley Field: November 20–December 31
Christmas returns to Gallagher Way outside Wrigley Field as Winterland and the Wrigleyville edition of Christkindlmarket open for the season on November 20. Visitors can shop for handmade gifts and ornaments, enjoy German-inspired food and seasonal drinks, and take in the neighborhood’s holiday decorations. The market is free to enter, while some Winterland activities have separate admission fees.
The planned Winterland attractions include outdoor ice skating, holiday train rides, Santa visits, seasonal photo opportunities and special events. A tree-lighting event is listed for Friday, December 4, from 6 to 8 p.m. Other programming and details may change as the season approaches.
Christkindlmarket regular hours: Monday–Thursday, 3–9 p.m.; Friday–Saturday, 11 a.m.–9 p.m.; Sunday, 11 a.m.–7 p.m. Holiday dates and late-December hours may differ. Official market information and Gallagher Way events calendar.
For a closer look at the market, see our earlier Christkindlmarket 2026 guide.
TBOX: The 30th Annual Twelve Bars of Xmas — December 12, 2026
The annual TBOX Christmas bar crawl celebrates its 30th anniversary on Saturday, December 12, 2026, with festivities beginning at 10 a.m. at The Cubby Bear. Participants dress in holiday costumes and ugly Christmas sweaters while making their way among participating Wrigleyville bars throughout the day.
This ticketed event features participating bars, food and drink specials, music, giveaways and longstanding TBOX traditions. Participants must be 21 or older. Some Wrigleyville venues may have special access restrictions during the crawl, so check individual bar policies before visiting. TBOX tickets and details.
Planning your Wrigleyville Christmas outing
The holiday attractions are concentrated around Gallagher Way and the Clark Street entertainment district, making it possible to combine shopping at Christkindlmarket, photos outside Wrigley Field and a visit to one or more holiday-themed bars. Weekends and special events such as TBOX can draw large crowds; check each bar’s schedule, reservations, ticket requirements and age restrictions.
We’ll continue updating this Wrigleyville Christmas 2026 guide as additional bars announce opening dates and holiday activities are finalized.