Best Holiday Cocktails in Historic Chicago Bars

We want to share some of the best holiday cocktails in Chicago’s historic bars with you! It’s been a blast exploring Chicago’s holiday traditions on our annual Virtual Holiday Stories Happy Hour. Our guests have especially enjoyed the holiday cocktails (and other drinks) available during the tour. That got us thinking. The spirit of giving defines this time of year, so here we give you some of the best holiday cocktails to enjoy in our historic Chicago bars!

While you’re here, check out our Badass Women Journal and Virtual Holiday Stories Happy Hour. The former is perfect for gift-giving and the latter is a wonderful way to spend time with family and friends this holiday season.

holiday tour drinks daleys dead guys holiday cocktails tom and jerry

Tom & Jerry at Miller’s Pub

Cocktail number one is a star attraction on our Holiday Tour of Drinks, Daleys and Dead Guys. The Tom & Jerry at Miller’s Pub is a classic cocktail and perfection during the brisk Chicago holiday season. For the uninitiated, a Tom & Jerry is a warmed cocktail. The bartender spikes what is essentially eggnog, that beloved Christmas staple, with both rum and brandy. As you can see above, the Tom & Jerry at Miller’s Pub is served piping hot in a mug.

Miller’s Pub is one of the most famous, and long-lasting, historic bars in downtown Chicago. It (sort of) dates back to 1935 and you’d have to come on our Holiday Tour to better learn its history (wink, wink). This historic Chicago bar has been a popular hangout for everyday Chicagoans and big-name visitors like Marilyn Monroe and Jay Leno. Personally, I’ve always loved the old-fashioned decor and atmosphere in there. It’s also right downstairs from where the Chicago Detours office used to be, so I got to know it fairly well.

Glühwein at Christkindlmarket

Is it cheating to include spiced wine at a seasonal outdoor market in this list? Probably. But I don’t care! This is simply too essential a part of the holiday experience in Chicago. Glühwein is a warmed, mulled wine that’s long been a part of the holiday season traditions in Germany. It’s become a similarly big tradition for the countless people who visit Christkindlmarket, Chicago’s faux-German Christmas village. Now, what goes into Glühwein?

Maybe they’ll have a better ingredients list this year? Regardless, Glühwein is super delicious and well worth the endless elbowing that makes up much of a visit to Christkindlmarket.

Glögg at Simon’s

If we’re including Glühwein, then it’s only fair to mention glögg, Chicago’s other famous mulled holiday wine. Like Glühwein, glögg mixes port wine with raisins and mulling spices. The best recipes call for the glögg to steep for an hour before heating and serving. Swedes of all ancestries have been glugging glögg at Simon’s for nearly a century. Simon’s, a legendary dive bar in Andersonville, never lost touch with the old world drinking habits that now show up as speciality holiday cocktails.

The drinks are served with a side of fascinating history. The bar’s founder, Simon Lundberg, is a legend in Andersonville. In his time, Lundberg and his family sold groceries, cashed paychecks, and served “coffee” for mobsters during Prohibition. Simon himself operated a coffee-free speakeasy called the “No Name Club” out of the basement. (P.S. Apparently if you can spot five animals hidden in their mural you get to wear the bar’s Viking helmet for the rest of the night. Fun!)

Santa’s Cranpeppy at The Cove

Once upon a time, your author here spent a good many nights at the Cove, a classic dive bar in Hyde Park. My friends and I discovered this historic Chicago bar while enrolled at the University of Chicago. It wasn’t an “every night” sort of place (no time for that). But after big assignments or deadlines, it was a great place to meet up and hang out for hours over cheap drinks. No longer being in need of commiseration after a term paper, I reached out to the Cove to discover if they had any holiday cocktails.

Friends, it’s a doozy. Santa’s Cranpeppy mixes 1.5 oz of Rumple Minze peppermint schnapps with a splash of carbonated cranberry juice and serves it on the rocks. That sounds perfectly Christmas-y and delicious. In fact, I may be planning a trip down to Hyde Park before my family gets into town.

Holiday Cocktails Santa's Hot Mug Happy's Chicago Athletic Association Hotel Land and Sea Dept.
Santa’s Hot Mug is a holiday cocktail served at Happy’s in the CAA. Photo by Lyndon French.

Santa’s Hot Mug at Happy’s

Santa is apparently moonlighting as a holiday cocktails bartender this year! He whipped up the Cranpeppy at the Cove and then whisked up to Happy’s, the holiday-themed pop-up bar at the Chicago Athletic Association Hotel. The CAA is, of course, where we end our 1893 World’s Fair Tour with Bars. The fabulous Venetian Gothic architecture from 1893 defines its 2nd-floor bars. Happy’s, on the ground floor, is the latest in a series of pop-up bars and events that the CAA has hosted since re-opening. When I stopped in a few weeks ago it was a bustling, festive space filled with revelers.

Santa’s Hot Mug, created by the cocktail maestros from Land and Sea Dept., is a delicious holiday treat. Served in a souvenir mug that you get to keep (!), the drink mixes hot chocolate with Cynar and mint. Before you go diving to Google, I had to look up Cynar as well. It’s a bittersweet Sicilian liquer distilled from artichoke (among other things). The end result, of course, is a cozy and delicious drink that’s perfect after a blustery walk down Michigan Avenue.

Got other holiday cocktails that we should sample? Send us a message on social media or email us at And we hope your holiday cocktails are delicious and the historic atmosphere is grand!

– Alex Bean, Content Manager and Tour Guide


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
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Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
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Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
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