7 Festive Holiday Bars to Visit in Chicago This Winter

Chicago takes holiday cheer seriously and nowhere is that more obvious than its bar scene. Each December neighborhood classics and pop-ups alike transform into festive wonderlands serving up themed cocktails and over-the-top décor. Here are seven festive bars to add to your Chicago holiday bucket list.

For more Chicago-specific holiday fun, be sure to check out our complete Chicago Holiday Guide!

1. Butch McGuire’s

A Chicago icon since the 1960s, Butch McGuire’s is the OG holiday bar. Every inch of the space is covered in garlands, lights and ornaments making it one of the city’s most nostalgic traditions.

2. Rudolph’s Christmas Bar

Located in River North, Rudolph’s is a full-on holiday takeover with neon décor, themed drinks and Instagram-worthy photo ops. It is playful, festive and right in the heart of downtown.

3. 8 Crazy Nights at Graystone Tavern

Chicago’s only Hanukkah-themed pop-up, 8 Crazy Nights features dreidel games, latkes and blue-and-white lights. The cocktails are as creative as the décor making it a fun and unique twist on the holiday bar scene.

4. O’Donovan’s

This North Center neighborhood spot transforms every December into a cozy festive hangout. Known for hearty food and laid-back vibes, it is perfect if you want holiday cheer without the downtown crowds.

5. Elf’d Up

Wrigleyville’s Elf’d Up pop-up is inspired by the movie Elf and brimming with themed cocktails, life-sized cutouts and playful décor. It is kitschy, colorful and guaranteed to make you smile. BUDDY THE ELF, WHAT’S YOUR FAVORITE COLOR?!

6. The Christmas Club

Also in Wrigleyville, The Christmas Club is three floors of holiday overload complete with themed rooms, dancing and cocktails served in ornament-style glasses. It is part nightclub, part holiday playground.

7. Frosty’s Christmas Bar

Lincoln Park’s Frosty’s is one of Chicago’s most over-the-top holiday pop-ups. With DJs, dancing and lights covering every wall, it feels like a holiday party exploded in the best way possible.

✨ Little Escapes Co. Tip: These holiday bars get busy especially on December weekends. For the best experience go early in the evening or on a weekday when the crowds are lighter and lines move faster. Also, make sure to stay festive and wear your favorite holiday sweater! We're loving this Buddy the Elf sweater , Candy Cane sweater and this Christmas Vacation themed sweater to get in the holiday spirit.

Rudolph’s Christmas Bar with our Buddy the Elf themed sweaters!

Plan the Rest of Your Festive Chicago Weekend 🎄

Holiday bars are just one way Chicago shines in the winter. From skating under the skyline to shopping festive markets and exploring twinkle-light trails there is so much more to do. To make planning effortless, download the Chicago Holiday Escape Mini Guide, a 10-page PDF with holiday highlights, shopping spots, festive dining and drinks, weekend holiday activities, event dates and a winter packing list to make sure you stay warm in Chicago.

👉 Get the Chicago Holiday Escape Mini Guide here.

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