Looking for festive vibes and seasonal cocktails? These Chicago bars are decking the halls with unique drinks, cozy decor and plenty of holiday spirits. Whether you’re seeking an over-the-top pop-up or a low-key spot with seasonal flair, here’s where to celebrate.
READ MORE: Best Holiday Pop-Ups for Festive Fun
Rudolph’s Bar
The Scoop: A Chicago holiday classic, Rudolph’s in Wrigleyville brings a sleigh-full of festive magic with twinkling lights, intimate nooks and over-the-top seasonal decor. Sip on holiday-themed cocktails like spiked eggnog, peppermint martinis or a warm mulled wine as you soak up the atmosphere. Perfect for an Instagram-worthy night out or a cheerful pre-dinner drink.
The Redhead Piano Bar
Why Go: Sing your heart out with nightly live piano music and holiday carol sing-alongs at The Redhead Piano Bar in River North. This late-night spot is the epitome of wintry vibes, with garlands, mistletoe and a limited-time holiday cocktail menu. Try the candy cane (vanilla vodka, Bailey’s, and peppermint schnapps), jingle juice (bourbon, cranberry juice, ginger ale), or the Kris Kringle kir royale (cranberry juice, Chambord, and Korbel). Buying a holiday cocktail in December scores a raffle ticket, with a nightly drawing for a chance to join the pianist on stage.
She-nannigans
What to Expect: A hub for festive fun, She-nannigans in Gold Coast hosts Holiday Game Nights with festive board games, darts and giant Jenga, alongside a DJ spinning seasonal hits Thursday through Sunday. The bar is decked out with holiday decor, adding to the merry atmosphere. Sip on drinks from a holiday menu with unique twists on classic cocktails. Thursdays are for Holiday Carol-oke at 8 p.m., and on Friday, Dec. 20, don your quirkiest attire at the Ugly Sweater Holiday Party at 7 p.m.
The Lodge Tavern
Why It’s Festive: Already a cozy spot year-round, Division St.’s Lodge transforms into a winter cabin wonderland for the holidays, with garlands, wreaths and twinkling lights. From the bar, enjoy festive drinks like the ho ho hot toddy or St. Nick’s cider, or warm up with holiday beers on tap. Ideal for a casual night out or post-shopping unwind.
Mariah Carey’s Holiday Bar
Must-Visit: Virgin Hotels and Bucket Listers team up with the “Queen of Christmas” herself to create a whimsical pop-up experience. Running Nov. 15 – Dec. 29, this bar features over-the-top holiday decor, whimsical photo ops and interactive elements like a “letters to Mariah” station. Don’t miss the drinks menu, featuring festive concoctions made with Mariah Carey’s Black Irish liqueur.
Pippin’s Tavern
Belly Up: River North’s Pippin’s Tavern has magic to do this season with a full transformation into a winter wonderland. Guests can enjoy specialty seasonal cocktails, holiday beers on tap and festive specials throughout December. Swing by for Happy Hour, Monday through Friday, 3–6 p.m., for deals like $1.50 oysters, $6 draft beer and buy-one-get-one small plates. A perfect way to kick off an evening of holiday revelry.
