Restaurants with the Best Holiday Cocktails in Chicago

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What’s a holiday without some of the best holiday-themed winter cocktails in Chicago, right? It’s cold outside, and nothing beats a spiked hot chocolate or a classic hot toddy. Therefore, we’ve asked around and gathered what we think are the best holiday cocktails in Chicago this year. Cinnamon, chocolate, Jell-O, cider… so many options, I guess we’ll have to try them one by one!


3335 N Halsted St, Chicago, IL 60657

Located in Chicago’s Northalsted neighborhood, the Six-Time Michelin Bib Gourmand winner is offering the ultimate “Whiskey Hot Cider” to pair with menu items and keep you warm and cozy.

  • Whiskey Hot Cider – tullamore dew irish whiskey, klug farm unfiltered apple cider, cinnamon bark, orange peel

seasonal cocktails in chicago press room
Image Credit: The Press Room

The Press Room

1134 W Washington Blvd, Chicago, IL 60607

Located in Chicago’s West Loop neighborhood, The Press Room is the ultimate speakeasy serving sophisticated but familiar food, friendly wines and classic cocktails. This winter, diners can sip on their housemade Hot Cider while listening to live music or enjoying date night. Looking to make cocktails at home? The Press Room is now selling their Gluhwein for pick-up orders on Tock.

Sold in a 32 oz crowler for $30.00, this is the perfect at-home cocktail!

  • Hot Cider – Bourbon & Calvados, cranberry bitters, lemon expression and michigan cider mulled with allspice, cinnamon, nutmeg, clove, peppercorn, sea salt and orange

  • Gluhwein – Cinnamon, Clove, Cardamom, Allspice, Orange

El Che Steakhouse & Bar

845 W Washington Blvd, Chicago, IL 60607

El Che Steakhouse and Bar is stepping up their game with brand new holiday cocktails this year, in addition to their iconic winter Spritz, which is definitely one of our favorites. So bring a friend, so you can check out both!

  • Winner Winner After Dinner – Averna Amaro, Yellow Chartreuse, Coffe and Hand Whipped Cream
  • La Fuerza Vermu Spritz – with housemade tonic syrup, soda and fresh rosemary

8 Crazy Nights

3441 N Sheffield Ave, Chicago, IL 60657

The Hannukah bar pop-up at The Greystone Tavern is nothing but holiday cocktails! Our favorite is the Gelt Martini, with Dorda Double Chocolate, 28 Mile Vodka, Tippy Cow Chocolate Shake in a martini glass rimmed with gold sugar or powdered sugar and a gelt coin garnish.

And don’t forget to check out the rest of the menu!

rambler holiday cocktail silver gold
Image Credit: The Rambler Kitchen and Tap


4128 N Lincoln Ave, Chicago, IL 60618

Have you heard? Rambler is turning into Misfit Christmas this holiday season. Dedicated to recalling old memories and honoring a childhood classic, Misfit Christmas’s drink menu is equally iconic and nostalgic, transporting you into the holiday decorations you remember from the old days.

  • Silver and Gold – NOLET’S Silver Gin, Mionetto Prosecco and white cranberry juice with a cranberry and rosemary garnish
holiday drinks in Chicago coffee spiked
Image Credit: Rewired Pizza & Cafe

Rewired Pizza Bar & Cafe

1100 W Thorndale Ave, Chicago, IL 60660

To help guests warm up and stay festive this holiday season, Rewired offers a Yulelog Fire Much with smoked peppermint chocolate sauce, espresso, and milk. It’s topped with crushed peppermint and toasted marshmallow. Guests can enjoy a non-alcohol version of the drink, or add their favorite alcohol like Journeyman Coffee Liqueur for an up-charge.

Farm Bar

1300 W Wellington Ave, Chicago, IL 60657

Who doesn’t love Farm Bar? They literally have one of the best seasonal menus all the time. However, have you checked out their seasonal cocktail menu? Because we’re loving it — from the smart word plays to the delicious taste!

  • Rum Rum Reindeer – Chicago Spirits Rum, House Made Cranberry & Lemongrass Syrup, Lime, Mint, and Soda Water
  • Sleigh All Day – Florence Field Gin, Pimento Dram, House Mulled Wine
  • Son of a Nutcracker – RhineHall Apple Brandy, Praline Syrup, Hot Cocoa, House Whipped Cream

The Smith

400 N Clark St, Chicago, IL 60654

Located in Chicago’s River North neighborhood, The Smith is the perfect spot to enjoy a delicious meal and hot beverage before heading to holiday festivities. New to the menu this winter, diners can sip on:

  • Hot Toddy –  bourbon / tawny port / lemon / bitter orange / honey / cinnamon

  • Spiked Hot Chocolate  – bourbon / hazelnut / chocolate liqueur / coconut / whipped cream

  • Hot Apple Cider –  add bourbon or spiced rum (add bourbon or spiced rum +$8)

The Dearborn

145 N Dearborn St, Chicago, IL 60602

Located in Chicago’s Loop neighborhood, The Dearborn is the perfect spot to enjoy a meal and specialty cocktails before walking over to the Christkindlmarket or Maggie Daley Park to ice skate. New to the menu, diners can sip on Gluhwein or a Boozy Hot Chocolate.

  • Gluhwein – mulled red wine, brandy, ruby port, lemon, orange, allspice, cinnamon, clove, star anise, golden raisins, dried apricots

  • Chef Julianna’s Hot Chocolate – steamed to order, homemade marshmallows {add a dram shot of Rumchata 1oz} +5

FireLake Grill House & Cocktail Bar

221 N Columbus Dr, Chicago, IL 60601

Digging the Christmas vibe? Come check out the seasonal drink menu at FireLake — specifically, the Grinch cocktails! You can also build your own wine flight by choosing any 4 wines from their extensive list of reds, whites, and bubbles.

  • Mexican Campfire – Los Vecinos Mezcal, agave, Aztec chocolate bitters, smoke
  • The Grinch Sour – Tito’s, midori, triple sec, coconut cream, lime, soda (serves two)
  • After Hours in Whoville – Evan Williams bourbon, blue curacao, apple cider, holiday syrup, lemon, champagne (serves two)

Replay Lincoln Park

2833 N Sheffield Ave, Chicago, IL 60657

All month long, the bar will transform its main room to replicate Hogwarts at Christmastime, with several photo opportunities with iconic characters and scenes from the popular series, such as the Great Hall, decked out in all of its festive glory, with wreaths, garland, candles, and snow. The pop up will feature thematic, seasonal drinks such as Dementor’s Kiss, Polyjuice Potion, Rowena’s Diadem, shots of Voldemalort, and more!

Houndstooth Saloon

3369 N Clark St, Chicago, IL 60657

Did you check out our list of holiday pop-ups happening around the town? Then you know Houndstooth Saloon is doing some awesome things thing this year with, of course, some of the best holiday cocktails! The lively Wrigleyville country bar has transformed into a holiday wonderland with wall-to-wall décor inspired by the film “National Lampoon’s Christmas Vacation”, so come check it out!

  • Aunt Bethany’s Jell-O Mold Fishbowl – Absolut Watermelon, green Jell-O, and Aunt Bethany’s cat food
  • Cousin Eddie’s Eggnog – housemade with brandy

Featured Image Credit: The Dearborn

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