There might be no season Chicago’s nightlife scene is better suited for than the holidays. Something about the festive, frigid atmosphere paired with the town's bevy of quaint, comforting pubs and restaurants creates a magical atmosphere for those looking to celebrate the Christmas spirit out on the town.
Luckily enough, Chicago’s food and drink scene seems to agree, with many of the best places around the Windy City embracing the seasonal cheer with open arms. Festive decorations, intricate light displays, and inviting seasonal bites and sips are just some of the fun stops Chicago establishments break out to attract customers during this busy time. However, with the endless amount of options at Chicagoans’ fingertips, it can be difficult, bordering on overwhelming, to choose where to dine out or stop for a drink.
So with boots firmly on the ground, Chicago Star highlights a few of our favorite bars and restaurants across town that can’t be missed during this holiday season.
Photo by David Cohn
Corcoran’s Pub & Grill
This long-time Irish pub favorite is best known for its St. Patrick's Day shenanigans, but that doesn't mean they don’t show similar love for Christmas. Run by Vaughs Hospitality, which operates a number of Irish pubs across Chicago, Corcoran’s cozy, wood-paneled aesthetic and spacious heated patio are elevated with beautifully crafted holiday decorations to create the perfect watering hole for a cold December night. Delicious pub fare, along with specialty seasonal cocktails, adds the cherry on top that makes this Windy City staple a go-to during the Christmas season.
Photo by David Cohn
Mary Jo Maguire’s
A new face with old history, Mary Jo Maguire opened their doors this fall just in time to get into the Christmas Spirit. As the sister restaurant to famed Division Street landmark Butch Maguire's, Mary Jo’s comes from Chicago pub royalty and strives to live up to that name in more ways than one. Featuring a two-story space, the first floor of the establishment takes a more saloon style approach that echoes the feel of the original Butches, while the second story offers a stage for music acts and performances that elevate the new location and embrace the artistic traditions of its Lincoln Street home.
Named after Butch Maguire's beloved wife, and opened by two of his grandsons, Mary Jo’s has transformed its space for the Christmas season with ornament-lined trees, top-to-bottom lighting, garland, mistletoe and more. For those who take pride in their Chicago nightlife and are looking to try something new this holiday season, Mary Jo’s is a must-add to the list.
Photo by: The Broken Barrel Bar
The Broken Barrel Bar
This Lincoln Park sports bar has been a go-to spot for Chicagoans' tailgating needs since 2018. Featuring a scratch-made menu and unique cocktails, Broken Barrel is accentuated by its 2000 ft. beer garden, heated in the winter for year-round enjoyment. The restaurant has always taken pride in its decor, hiring a number of local artists to provide pieces throughout the years, and the same attitude is taken during the Christmas season. Patrons of The Broken Barrel will be treated to incredible decorations, including oversized presents, Christmas trees, mistletoe, and even a giant sleigh pulled by Santa that is sure to deliver a unique and unforgettable dining experience.
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Photo by: Winnies
Winnie’s
The newest entry on this list, Winnies, arrives on the Wells Street bar scene, bringing fresh flavors and a down-home atmosphere to the heart of Old Town. Recently opened in November, Winnies combines a classic sports bar feel with a menu designed around health-forward bar bites and cocktail favorites that create a pub that evokes both a contemporary yet familiar ambiance. Started by local resident and first-time bar owner Chris Boutros, Winnies is already showing veteran instincts, embracing the Christmas season with festive holiday drinks, and welcoming decor that offers a little something for everyone. Spread the Christmas spirit this winter by supporting local businesses and checking out this brand new establishment before it becomes the talk of the town.
With students out of school and adults off work, it is no wonder the holidays remain one of the most popular times for both locals and visitors alike to hit the town in Chicago. And with an impending cold winter ahead, it's never been more important to find a good watering hole to stay warm at, so check out one of these great locations for festive food, cocktail classics, and celebratory atmospheres this Christmas season!







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