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Courtesy of The Bassment

Chicago’s Most Festive Spots for the Winter

It’s the most wonderful time of the year — for a rum cocktail in a cozy bar.

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Winter may be upon us, but there’s no reason to stop feeling festive — just head to your local bar. Chicago is home to several that are offering plenty of ways to celebrate the season, including heated igloos, charity drives, — and, of course, the perfect cocktails for season. Here, we share 10 bars that are bound to get you into the festive spirit, stat.

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Note: Restaurants on this map are listed geographically.
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90 Miles Cuban Cafe

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It’s easy to spot the merriment at this Cuban restaurant. Find the perfect one, but only after a sampling of seasonal favorites inside (i.e. eggnog empanadas). Bring your own booze to that outpost, or head to its Lincolnwood location for a full bar of wintertime tipples — namely the Cuban Eggnog (with BACARDÍ Superior, cream of coconut, and cinnamon). Feel good while fueling up here: Those who bring a canned good or toy for their December drives can enjoy 20 percent off the bill.

Courtesy of 90 Miles Cuban Cafe

Hubbard Inn

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Fans of wizardry and wintertime festivities alike are in good hands at this River North bar, which is transforming into a Harry Potter pop-up tribute through the start of winter. The magic culminates on December 22, when a formal Yule Gala will feature extravagant seasonal décor (a la the Yule Gala in Harry Potter and the Goblet of Fire), ranging from icicles and snowflakes to ice sculptures and firepits. Enjoy it all while sipping on the perfect cold-weather accompaniment — the Spiced Winter Delight packs in BACARDÍ Oakheart, apple cider, ginger beer, and toasted marshmallow.

El Hefe Chicago

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Escape to tropic temperatures come cooler months with a visit to this River North restaurant, a neighborhood favorite for south-of-the-border staples like chicken tinga tacos, queso fundido, and carne asada. You’ll find plenty of festive décor, and, of course, good drams — including $4 BACARDÍ drinks.

The Hampton Social

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This Hamptons-inspired spot takes guests to a winter beach escape come January, when its swinging hammocks and Adirondack chairs are met with lavish déécor, sparkling lights, and flowing strands of garland. Warm up with a round of Nana’s Spiked Cider (a rich and boozy serving of dark rum, banana liqueur, and spiked cider) before sharing a few of the venue’s East Coast signatures, including clam chowder, lobster rolls, and fish and chips.

The name of this Latin American restaurant translates to “one who has mastered the art of distilling rum” — as such, expect only the finest expressions of the spirit by way of bottle selections and cocktails, from the piña colada (with BACARDÍ Superior, coconut, pineapple, and fresh cream) to the Hotel Nacional (with rum, apricot liqueur, pineapple, and lime). Those drams are all the more decadent come winter, when the team honors the Colombian Festival of Flowers via a lush spread of floral arrangements and tropical wreaths. Visit on Thursdays for Tumbao LIVE, a weekly display of some of the city’s hottest Latin bands.

Ben Macri

Joy District Chicago

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For a taste of the season in the heart of downtown, head to this River North bar, which is outfitted with large ornaments, twinkling lights, and great lengths of garland. Sip through a medley of festive drinks, from the Caribbean Holiday (with BACARDÍ Banana, pineapple, lime, and pear liquor) to the Sugar Plum Rum (with BACARDÍ, Winter Edition Plum Red Bull, and lime). For the ultimate snow day sanctuary, book a private igloo on the rooftop — the team here is transforming it into a winter wonderland rife with the heated retreats (complete with string lighting and ornaments aplenty).

Bracket Room

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This sports bar pours 40 beers on tap every day of the week, ensuring variety and good vibes for an array of occasions. For the winter season, the behind the bar approach turns slightly more spirited with several concoctions, including eggnog (with BACARDÍ Black, nutmeg, and whipped cream) and peppermint martinis (with BACARDÍ, peppermint schnapps, crème de cacao, and a candy cane garnish).

Courtesy of Bracket Room

Roscoe's

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This neighborhood hangout has been dazzling Lakeview denizens and visitors alike for more than 30 years with friendly service, solid drink specials, and a robust calendar of events (think karaoke competitions and dueling piano nights). That hospitality is only heightened during the winter, when the team bedecks the space in seasonal flair and offers a lineup of festive libations, such as BACARDÍ Limon lemon bar, spiced apple, or cranberry cocktail Jell-O shots.

Courtesy of Roscoe’s

Butch McGuire's

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Ample seasonal displays have been a signature draw for this Gold Coast bar since the late ‘60s — ever since its owner purchased all of Goldblatt’s window displays to cover the ceiling. The same dedication to décor is intact today, with a few festive additions: an annual toiletry drive, sponsored toy trains circulating the space, and for-sale ornaments benefiting The Mercy Home for Boys and Girls. Couple that cheer with any of the bar’s specialty drinks — especially the Division Street Pop, with BACARDÍ Oakheart, Cointreau, Averna, and soda.

Courtesy of Butch McGuire’s

Bassment

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Strung garland, lights, and wreaths decorate this underground dance destination come the winter — a particularly good time to catch its vast range of live music talent from local acts. Enjoy those tunes with any of the bar’s original cocktails, such as the Stevie Nicks (with apple liqueur and butterscotch) or the Elton John (with spiced wine and apple cider). And snag a few of the venue’s spirit-infused cigars while you’re there.

Jennifer Catherine Photography
This advertising content was produced in collaboration between Vox Creative and our sponsor, without involvement from Vox Media editorial staff.

90 Miles Cuban Cafe

Courtesy of 90 Miles Cuban Cafe

It’s easy to spot the merriment at this Cuban restaurant. Find the perfect one, but only after a sampling of seasonal favorites inside (i.e. eggnog empanadas). Bring your own booze to that outpost, or head to its Lincolnwood location for a full bar of wintertime tipples — namely the Cuban Eggnog (with BACARDÍ Superior, cream of coconut, and cinnamon). Feel good while fueling up here: Those who bring a canned good or toy for their December drives can enjoy 20 percent off the bill.

Courtesy of 90 Miles Cuban Cafe

Hubbard Inn

Fans of wizardry and wintertime festivities alike are in good hands at this River North bar, which is transforming into a Harry Potter pop-up tribute through the start of winter. The magic culminates on December 22, when a formal Yule Gala will feature extravagant seasonal décor (a la the Yule Gala in Harry Potter and the Goblet of Fire), ranging from icicles and snowflakes to ice sculptures and firepits. Enjoy it all while sipping on the perfect cold-weather accompaniment — the Spiced Winter Delight packs in BACARDÍ Oakheart, apple cider, ginger beer, and toasted marshmallow.

El Hefe Chicago

Escape to tropic temperatures come cooler months with a visit to this River North restaurant, a neighborhood favorite for south-of-the-border staples like chicken tinga tacos, queso fundido, and carne asada. You’ll find plenty of festive décor, and, of course, good drams — including $4 BACARDÍ drinks.

The Hampton Social

This Hamptons-inspired spot takes guests to a winter beach escape come January, when its swinging hammocks and Adirondack chairs are met with lavish déécor, sparkling lights, and flowing strands of garland. Warm up with a round of Nana’s Spiked Cider (a rich and boozy serving of dark rum, banana liqueur, and spiked cider) before sharing a few of the venue’s East Coast signatures, including clam chowder, lobster rolls, and fish and chips.

Ronero

Ben Macri

The name of this Latin American restaurant translates to “one who has mastered the art of distilling rum” — as such, expect only the finest expressions of the spirit by way of bottle selections and cocktails, from the piña colada (with BACARDÍ Superior, coconut, pineapple, and fresh cream) to the Hotel Nacional (with rum, apricot liqueur, pineapple, and lime). Those drams are all the more decadent come winter, when the team honors the Colombian Festival of Flowers via a lush spread of floral arrangements and tropical wreaths. Visit on Thursdays for Tumbao LIVE, a weekly display of some of the city’s hottest Latin bands.

Ben Macri

Joy District Chicago

For a taste of the season in the heart of downtown, head to this River North bar, which is outfitted with large ornaments, twinkling lights, and great lengths of garland. Sip through a medley of festive drinks, from the Caribbean Holiday (with BACARDÍ Banana, pineapple, lime, and pear liquor) to the Sugar Plum Rum (with BACARDÍ, Winter Edition Plum Red Bull, and lime). For the ultimate snow day sanctuary, book a private igloo on the rooftop — the team here is transforming it into a winter wonderland rife with the heated retreats (complete with string lighting and ornaments aplenty).

Bracket Room

Courtesy of Bracket Room

This sports bar pours 40 beers on tap every day of the week, ensuring variety and good vibes for an array of occasions. For the winter season, the behind the bar approach turns slightly more spirited with several concoctions, including eggnog (with BACARDÍ Black, nutmeg, and whipped cream) and peppermint martinis (with BACARDÍ, peppermint schnapps, crème de cacao, and a candy cane garnish).

Courtesy of Bracket Room

Roscoe's

Courtesy of Roscoe’s

This neighborhood hangout has been dazzling Lakeview denizens and visitors alike for more than 30 years with friendly service, solid drink specials, and a robust calendar of events (think karaoke competitions and dueling piano nights). That hospitality is only heightened during the winter, when the team bedecks the space in seasonal flair and offers a lineup of festive libations, such as BACARDÍ Limon lemon bar, spiced apple, or cranberry cocktail Jell-O shots.

Courtesy of Roscoe’s

Butch McGuire's

Courtesy of Butch McGuire’s

Ample seasonal displays have been a signature draw for this Gold Coast bar since the late ‘60s — ever since its owner purchased all of Goldblatt’s window displays to cover the ceiling. The same dedication to décor is intact today, with a few festive additions: an annual toiletry drive, sponsored toy trains circulating the space, and for-sale ornaments benefiting The Mercy Home for Boys and Girls. Couple that cheer with any of the bar’s specialty drinks — especially the Division Street Pop, with BACARDÍ Oakheart, Cointreau, Averna, and soda.

Courtesy of Butch McGuire’s

Bassment

Jennifer Catherine Photography

Strung garland, lights, and wreaths decorate this underground dance destination come the winter — a particularly good time to catch its vast range of live music talent from local acts. Enjoy those tunes with any of the bar’s original cocktails, such as the Stevie Nicks (with apple liqueur and butterscotch) or the Elton John (with spiced wine and apple cider). And snag a few of the venue’s spirit-infused cigars while you’re there.

Jennifer Catherine Photography

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