Holiday Cocktailing: The Best Spots to Check Out For Festive Holiday Cheer

via Fairmont Chicago

The holiday season is in full swing. It’s the most wonderful time of the year! It’s also freezing outside, which means we all need some fun distractions to get us through the next few months. Luckily, the options for a fun, festive vibe in Chicago are plentiful. Whether you’re in the mood for a holiday cocktail, or you want to check out some fun decor, we’ve got you covered!

The Fairmont Lodge at Fairmont Chicago, Millennium Park {200 North Columbus Drive, Chicago, IL; 312.565.8000}

‘Tis the season to be cozy! The Fairmont Chicago has transformed its hotel lobby into an alpine-inspired escape called the “Fairmont Lodge”.  It’s the perfect spot to go to feel like you’ve actually been transported to some glamorous mountain town far, far away. You can enjoy handcrafted cocktails alongside some really creative “culinary packages,” which is certainly a fun experience for an evening out on the town. The lodge is leaning into the après-ski vibes, meaning you can get house-made S’mores, charcuterie platters, or even a sweet or savory fondue. And there’s  live music Thursdays through Saturdays!

A Very Dandy Holiday Pop-Up at the Dandy Crown {694 North Milwaukee Avenue, Chicago, IL; 312.846.6420}

This fantastic pop-up has returned for the third year in a row, and it just gets better and better! A wide range of holiday-centric cocktails and mocktails are available in festive holiday glasses. We’re definitely eyeing the “Bing Crosby,” made with Don Q white rum, cocoa, peppermint and egg whites. If you’re permanently cold this winter, don’t worry, they have two hot cocktails to warm you up! The pop-up is open through Jan. 4, so you have plenty of time to check it out. Reservations are encouraged, but not required! 

via Three Dots and a Dash

Three Dots & A Dash: River North Pole Takeover {435 North Clark Street, Chicago, IL; 312.610.4220}

Chicago’s tropical oasis has transformed itself into the “River North Pole” for the holiday season, and we’re not mad about it! You can go enjoy one of their delicious cocktails in a winter wonderland, complete with a fun, festive glass, which makes it extremely instagram-worthy. Their holiday-themed drink menu includes a Mistletoe Mai Tai, an Eggnog Grasshopper, a Hot Buttered Rum, and even a Candy Cane Swizzle. As the bar says, “there’s holiday spirit in every sip!” 

The Mile High Cocktail Club at the Four Seasons Hotel Chicago {120 East Delaware Place, Chicago, IL; 312.280.8800}

If you’re feeling more glamorous this holiday season, be sure to book a night out at the Mile High Cocktail Club at the Four Seasons Chicago. Dress up in a fun winter outfit and embrace the cold! The high-end experience reopened in collaboration with Mexico City’s “Handshake Speakeasy,” which was just named the #1 bar in the world by The World’s 50 Best Bars.

The elevated lounge sits on the 46th floor of the hotel, making it the highest speakeasy in Chicago. Enjoy one of the signature cocktails by candlelight with a great view of the city. The Mile High Cocktail Club is open until March 1, and reservations are required!

Holiday Cocktails at Hawksmoor Chicago {500 North LaSalle Drive, Chicago, IL; 872.272.4240}

Head to the Hawskmoor Chicago to feel like you’ve stepped into a cozy British steakhouse! Located inside the historic LaSalle Cable Car Powerhouse in River North, you’ll immediately be given a warm welcome. Not only do they have delicious winter weather menu items like their Sunday Roast, but they have a whole new list of festive cocktails from their award-winning bar. We want to try “The Gingerbread,” which is a collab with NYC’s  famous bar “The Dead Rabbit”. It features Woodford Reserve Bourbon, Slane Irish Whiskey, Gold Rum and gingerbread spices. We also have our eye on the “Nauti Grasshopper,” created by the Scottish Bar Nauticus. It’s an elevated version of the typical grasshopper cocktail,  with Glendronach 12-year scotch whisky, mint, cacao, sage and cream. All these fun holiday cocktails are available through Dec. 31.

via Bar La Rue

Winter at Bar La Rue {820 West Fulton Street, Chicago, IL; 312.533.4607}

Fulton Market’s Bar La Rue is really leaning into its French inspiration this winter season! The space has been transformed into a cozy ski chalet, complete with winter florals, decor, a fire pit and even a genuine ski lift for those looking for a fun instagram story to post. In addition, they have a divine winter happy hour menu that includes cheese fondue service and bottomless frites. Cheese and fries, you can’t get much better than that! Oh, and their hot cocktails will warm you up fast this chilly winter season. The Jean Claude (bourbon, Benedictine, blackberry, mint and lemon) is to die for. They also have a spicy mulled wine for those who really want to get in the spirit. Bar La Rue is simply the perfect place to be cozy, while eating and drinking like the french après-ski! 

Winter Menu at Sofitel Chicago’s Le Bar {20 East Chestnut Street, Chicago, IL; 312.324.4000}

Spend an evening in luxury at Sofitel Chicago’s Le Bar this holiday season to really get into the festive spirit! There’s a new winter menu at Le Bar with cold weather-inspired cocktails, including a “Fireside Old Fashioned,” a “PSL Season” (Bacardi spiced rum, pumpkin pie syrup, lemon juice and egg white), and even a “Sweater Weather” mocktail, made with Seedlip Spice 94, spiced demerara, ginger beer and fresh lemon. We guarantee you will want to try multiple of these craft cocktails.

By Kerry Leary | Special Correspondent

Previous
Previous

Hot Spots to Ring in 2025 in Chicago

Next
Next

Christmas Meals from Chicago’s Restaurant Family