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Wrigleyville transforms into a festive wonderland each holiday season, offering some of the most exciting Christmas-themed bars in Chicago. Here’s your guide to the best spots to sip seasonal cocktails, snap Instagram-worthy photos, and soak in the holiday cheer.

1. Santa Baby Bar

Located at 3505 N Clark St., this over-the-top holiday pop-up offers multiple levels of Christmas-themed fun, including the Gingerbread Village and Rudolph’s Lounge. Expect whimsical decor, festive cocktails, holiday karaoke, and appearances by Santa himself. Reservations are recommended due to its popularity. Santa Baby also donates proceeds to local charities, so your holiday cheer contributes to a good cause.

2. Elf’d Up

Stretch Bar & Grill at 3485 N Clark St. transforms into an “Elf”-inspired holiday haven. Featuring Buddy the Elf-themed decorations, complimentary cookies, and playful cocktails like the Angry Elf Martini, this pop-up is a must for fans of the movie. Special menu items include Buddy’s Breakfast Pasta, making it a delightful nod to the classic film.

3. The Christmas Club

One of Wrigleyville’s original holiday bars, The Christmas Club (3460 N Clark St.) spans two floors with three themed party rooms and bars. Guests can enjoy themed cocktails, festive snacks, a live DJ, and even meet Santa. It’s open from November 22 through early January 2025.

4. 8 Crazy Nights at Graystone Tavern

This unique Hanukkah pop-up at 3441 N Sheffield Ave. celebrates Jewish traditions with over 8,000 blue and white lights, dreidel-themed decorations, and a menu featuring latkes, matzo ball soup, and vodka-infused boozy donuts. Signature cocktails include the Gelt Martini and Hanukkah Harry’s Hot Chocolate. Open November 27 through January 5, this is a refreshing addition to Wrigleyville’s festive scene.

5. Mistletoe at Hush Money

Located in Mordecai’s second-floor lounge, this chic pop-up offers sophisticated holiday cocktails like the cinnamon-horchata Santa’s Munchies. It’s perfect for a cozy yet festive night out.

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