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Calabaza en Tacha at WoodWind Nikki Allen Creative

8 Chicago Bars Where You Can Drink Holiday Rum Cocktails This Winter

Say hello to the holiday spirit (it’s rum, everyone)

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Anyone who spends the holidays in Chicago knows it’s not just cold — it’s downright freezing. But any Chicagoan also knows that won’t keep us from celebrating with friends and family, preferably at a bar or two. So why not warm yourself up while hanging with loved ones with a rum cocktail? It is the holiday spirit, after all. (Or at least, it should be.)

Grab some family and friends and head to these amazing Chicago bars that all feature delicious rum cocktails made with BACARDÍ, the premium spirit for holiday hangouts. Whether you’re looking for something lowkey and vibey or a place tailor-made for big groups, there’s something for everyone on this list of Chicago bars.

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WoodWind

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Located in Streeterville (18 floors above it, in fact), this contemporary American dining spot has everything you need when you’re looking for a good go-to spot. It has sophisticated — but not pretentious — dining and cocktails, regionally focused cuisine, and obviously, great views. It’s a bit of a hidden gem, located on the rooftop of the Northwestern Medical Campus (aka the top of the hospital), but it’s only blocks from Magnificent Mile. And while a rooftop may not scream “holiday,” the menu and inside digs definitely do. Make sure to try out a cocktail variation of the traditional Día de los Muertos dish Calabaza en Tacha, which WoodWind beverage director Carolina Gonzalez makes using candied pumpkin–infused BACARDÍ Ocho Sevillian Orange, brown butter–washed Santa Teresa 1796, piloncillo cane sugar, black walnut mist, and other autumnal ingredients that’ll have you feeling warm and fuzzy.

Calabaza en Tacha at WoodWind Nikki Allen Creative

Roscoe's Tavern

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This popular drag brunch spot has been open and thriving since 1987, with a dance floor, pool table, and outdoor spaces. It also has plenty of indoor space, including multiple bars, and is located in Northalsted aka Boystown. Come for the drinks and nightlife, come back for the movie viewings and musical bingo. As the weather turns colder, warm up indoors with the Old Cuban, made with BACARDÍ Reserva Ocho, mint, lime juice, bitters, and topped with sparkling wine. It’s an ideal place to dance the night away with friends in Boystown.

Old Cuban at Roscoe’s Tavern Nikki Allen Creative

El Che Steakhouse & Bar

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A short walk from “restaurant row” in the West Loop, this steakhouse takes cues from Argentinian asados with a menu of live-fire cooking and the country’s only 100-percent South American wine list. Whether you’re getting together with a big group of friends and ordering the 32-ounce party steak or having a more intimate affair, you can’t go wrong with the ambiance and food. Order your protein of choice and then put in an order for a Premium Rum Old Fashioned made with BACARDÍ Reserva Ocho Rye Cask, Santa Teresa 1796, jaggery sugar, pomegranate, and black walnut bitters. The warming, autumnal flavors pair beautifully with the savory steak. Salud!

the Premium Rum Old Fashioned at El Che Nikki Allen Creative

Warlord

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This Avondale restaurant is a collaboration from three veteran chefs and doesn’t take any reservations, so you can walk in to try your luck at nabbing a table Friday through Monday. The best part? It’s open late (2 a.m.) and serves food up to an hour until close (1 a.m.). The menu changes daily, focusing on what’s local and fresh, and is often cooked using live fire. The cocktail menu also changes regularly, but the bar team is also known for making a great classic as well. Try the Drunken Bean, made with BACARDÍ Reserva Ocho, Hexe Coffee, and Maplewood Coffee Liqueur.

the Drunken Bean at Warlord Nikki Allen Creative

The Giant Penny Whistle

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Live music events are the big draw at this Pilsen venue, but you can also grab a well-made drink at the vintage-inspired bar on the tavern side of the operation. With booths, a pool table, and a photo booth, the chill vibes in the tavern are best for hanging with friends and family and grabbing a round or two. Make sure to order a Tootsie Roll made with Santa Teresa 1796, Cynar, sweet vermouth, and Xocolatl mole bitters.

the Tootsie Roll at Giant Penny Whistle Nikki Allen Creative

Miki's Park

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For a fun hang in River North, hit this Korean-inspired bar serving casual bites and cocktails. With karaoke on Thursdays and Sundays and K-Pop nights on Fridays, this bar is the perfect mix of chill and lively. Try the BAD A$$ Teresita, made with Santa Teresa 1796, salted caramel syrup, and chocolate bitters, and don’t miss their chef-driven street food like the vegetarian Omma’s Dumplings and a Korean Red Hot topped with pickled slaw and gochu aioli.

BAD A$$ Teresita at Miki’s Park Nikki Allen Creative

The Hi-Lo

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This cocktail bar in Humboldt Park has both indoor and outdoor space (though as the weather changes, you’ll most likely be spending time inside), as well as a cocktail menu that’s split between “Hi” (standard-proof cocktails) and “Lo” (low-ABV cocktails). Open seven days a week, this gem of a place works equally well for catching up with friends, going on a cute date, or even just enjoying some alone time. As the temperatures dip, warm up with a hot cocktail like Spicy Pumps, the bar’s version of hot buttered rum with Santa Teresa 1796, walnut liqueur, and buttered spice syrup. Yum.  

Spicy Pumps at the Hi-Lo Nikki Allen Creative

Sportsman's Club

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Opened in 2013, Sportman’s Club is a modernized version of the Ukrainian Village dive bar that previously operated at its address. Remnants of that beloved spot still exist to this day, including the original art deco bar. The cocktail list, however, has gotten a glow-up — focusing on spirit-forward cocktails with both balance and simplicity, including the Blood Orange Espresso Tonic with Santa Teresa 1796, blood orange aperitivo, cafe de olla syrup, lemon, and tonic. Come for the classy drinks, stay for the company. Did we mention the bar also has an in-house amaro machine?

Blood Orange Espresso Tonic at Sportman’s Club Nikki Allen Creative
This advertising content was produced in collaboration between Vox Creative and our sponsor, without involvement from Vox Media editorial staff.

WoodWind

Located in Streeterville (18 floors above it, in fact), this contemporary American dining spot has everything you need when you’re looking for a good go-to spot. It has sophisticated — but not pretentious — dining and cocktails, regionally focused cuisine, and obviously, great views. It’s a bit of a hidden gem, located on the rooftop of the Northwestern Medical Campus (aka the top of the hospital), but it’s only blocks from Magnificent Mile. And while a rooftop may not scream “holiday,” the menu and inside digs definitely do. Make sure to try out a cocktail variation of the traditional Día de los Muertos dish Calabaza en Tacha, which WoodWind beverage director Carolina Gonzalez makes using candied pumpkin–infused BACARDÍ Ocho Sevillian Orange, brown butter–washed Santa Teresa 1796, piloncillo cane sugar, black walnut mist, and other autumnal ingredients that’ll have you feeling warm and fuzzy.

Calabaza en Tacha at WoodWind Nikki Allen Creative

Roscoe's Tavern

This popular drag brunch spot has been open and thriving since 1987, with a dance floor, pool table, and outdoor spaces. It also has plenty of indoor space, including multiple bars, and is located in Northalsted aka Boystown. Come for the drinks and nightlife, come back for the movie viewings and musical bingo. As the weather turns colder, warm up indoors with the Old Cuban, made with BACARDÍ Reserva Ocho, mint, lime juice, bitters, and topped with sparkling wine. It’s an ideal place to dance the night away with friends in Boystown.

Old Cuban at Roscoe’s Tavern Nikki Allen Creative

El Che Steakhouse & Bar

A short walk from “restaurant row” in the West Loop, this steakhouse takes cues from Argentinian asados with a menu of live-fire cooking and the country’s only 100-percent South American wine list. Whether you’re getting together with a big group of friends and ordering the 32-ounce party steak or having a more intimate affair, you can’t go wrong with the ambiance and food. Order your protein of choice and then put in an order for a Premium Rum Old Fashioned made with BACARDÍ Reserva Ocho Rye Cask, Santa Teresa 1796, jaggery sugar, pomegranate, and black walnut bitters. The warming, autumnal flavors pair beautifully with the savory steak. Salud!

the Premium Rum Old Fashioned at El Che Nikki Allen Creative

Warlord

This Avondale restaurant is a collaboration from three veteran chefs and doesn’t take any reservations, so you can walk in to try your luck at nabbing a table Friday through Monday. The best part? It’s open late (2 a.m.) and serves food up to an hour until close (1 a.m.). The menu changes daily, focusing on what’s local and fresh, and is often cooked using live fire. The cocktail menu also changes regularly, but the bar team is also known for making a great classic as well. Try the Drunken Bean, made with BACARDÍ Reserva Ocho, Hexe Coffee, and Maplewood Coffee Liqueur.

the Drunken Bean at Warlord Nikki Allen Creative

The Giant Penny Whistle

Live music events are the big draw at this Pilsen venue, but you can also grab a well-made drink at the vintage-inspired bar on the tavern side of the operation. With booths, a pool table, and a photo booth, the chill vibes in the tavern are best for hanging with friends and family and grabbing a round or two. Make sure to order a Tootsie Roll made with Santa Teresa 1796, Cynar, sweet vermouth, and Xocolatl mole bitters.

the Tootsie Roll at Giant Penny Whistle Nikki Allen Creative

Miki's Park

For a fun hang in River North, hit this Korean-inspired bar serving casual bites and cocktails. With karaoke on Thursdays and Sundays and K-Pop nights on Fridays, this bar is the perfect mix of chill and lively. Try the BAD A$$ Teresita, made with Santa Teresa 1796, salted caramel syrup, and chocolate bitters, and don’t miss their chef-driven street food like the vegetarian Omma’s Dumplings and a Korean Red Hot topped with pickled slaw and gochu aioli.

BAD A$$ Teresita at Miki’s Park Nikki Allen Creative

The Hi-Lo

This cocktail bar in Humboldt Park has both indoor and outdoor space (though as the weather changes, you’ll most likely be spending time inside), as well as a cocktail menu that’s split between “Hi” (standard-proof cocktails) and “Lo” (low-ABV cocktails). Open seven days a week, this gem of a place works equally well for catching up with friends, going on a cute date, or even just enjoying some alone time. As the temperatures dip, warm up with a hot cocktail like Spicy Pumps, the bar’s version of hot buttered rum with Santa Teresa 1796, walnut liqueur, and buttered spice syrup. Yum.  

Spicy Pumps at the Hi-Lo Nikki Allen Creative

Sportsman's Club

Opened in 2013, Sportman’s Club is a modernized version of the Ukrainian Village dive bar that previously operated at its address. Remnants of that beloved spot still exist to this day, including the original art deco bar. The cocktail list, however, has gotten a glow-up — focusing on spirit-forward cocktails with both balance and simplicity, including the Blood Orange Espresso Tonic with Santa Teresa 1796, blood orange aperitivo, cafe de olla syrup, lemon, and tonic. Come for the classy drinks, stay for the company. Did we mention the bar also has an in-house amaro machine?

Blood Orange Espresso Tonic at Sportman’s Club Nikki Allen Creative

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