Festive cocktails in Chicago: 7 bars for seasonal sipping

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There’s no better way to ward off the cold – particularly in snowy Chicago — than with a holiday drink.

Undoubtedly, one of our favorite things about the arrival of winter is the array of festive drinks. From warming mulled beverages to traditional eggnog and other spice-infused concoctions, there’s no better way to ward off the cold – particularly in snowy Chicago. We’ve rounded up seven Windy City cocktail bars we love, plus some suggestions for what to order on their festive, seasonal menus.

The Drawing Room

Hidden away underground, the Drawing Room is the perfect venue for some temporary hibernation. Of course, no winter hideaway would be complete without top-notch tipples. We recommend sampling from the accomplished, culinary-influenced cocktail list: The Loosened Belt, which blends Laird’s Apple Brandy, cranberry syrup, and walnut liqueur, is perfect for the season.

The Whistler

A combination gallery, music venue and bar, The Whistler in trendy Logan Square is festive enough to merit fighting through the snowy streets. The award-winning cocktail menu features an ever-changing drinks line-up. Try the Autumn Sweater, named for a Yo La Tengo song and perfectly seasonal: It blends autumnal gin, glögg (that’s Swedish mulled wine, for the uninitiated), bitters and lemon.

The Violet Hour

Named after a line in a T.S. Eliot poem, hip Violet Hour promises to provide a festive evening. The atmosphere is sophisticated yet fun — ideal for a night of merriment. Crown the celebrations off with a Sycamore Sling, which mixes Buffalo Trace bourbon, pear brandy, maple syrup and Douglas Fir eau de vie for a holiday kick.

The Violet Hour © Edsel Little
The Violet Hour © Edsel Little

The Aviary

At the Aviary, co-owned by VIP Chicago chef Grant Achatz, drinks are mixed in a state-of-the-art kitchen and are given the same attention to detail as dishes in a four-star restaurant. This splurge-worthy drinking den is ideal for a one-off, festive occasion. Note that its basement speakeasy, The Office, is also great for holiday tippling. 

The Aviary © Quinn Dombrowski
The Aviary © Quinn Dombrowski

Punch House

Punch is the original party drink, and at the newly opened Punch House they serve eight house-made punches every evening. What could better invoke the feeling of the holidays than that?

Punch House © mlwphotography/iStock/Thinkstock
Punch House © mlwphotography/iStock/Thinkstock


Chicago’s newest hipster dive bar may not seem like the place to indulge in a winter cocktail, but given that it’s run by two Violet Hour veterans, the drinks here have serious cred. Try the delectable Radio/Flyer, made with bourbon, lemon, smoked brown sugar and pumpkin bitters.

Bourbon cocktail © Edsel Little
Bourbon cocktail © Edsel Little

Lone Wolf

Customers can enjoy warming, freshly baked bar snacks along with an array of drinks at this brand new Chicago bar and restaurant, opened by the folks behind Pleasant House Bakery. Italian-inspired drinks, like the Seven Sisters (which mixes Fernet, Chartreuse and two amari) are rich and bitter cold-killers.

(Main image: © victoshafoto/iStock/Thinkstock)

Written by insider city guide series Hg2 | A Hedonist’s guide to… whose guides cover all the best hotels, restaurants, bars, clubs, sights, shops and spas

Festive cocktails in Chicago: 7 bars for seasonal sipping was last modified: June 26th, 2019 by Claire Bullen
Author: Claire Bullen (88 posts)

Globetrotter, chowhound, travel writer for Hg2 | A Hedonist’s guide to... and contributor to Cheapflights Travel Blogs.