The Best Chicago Drinks for Cold Nights

Winter can be pretty brutal around here. Personally, I think the best way to take the bite out of the frost is with a good drink. You can always do that on our Historic Chicago Walking Bar Tour or 1893 World’s Fair Tour with Bars. But I’m sure not everyone wants to go on a tour everytime they grab a drink. I’ve cast around with trusted co-workers and friends to come up with this list of great Chicago drinks for cold nights. And as we do with Chicago Detours, I added some history, too.

#1. Eugene Porter from Revolution Brewing

drinks for cold nights Chicago revolution brewing
A sampler flight at the Revolution Brewpub. Photo by Emilee Rader via flickr.

Worth noting that you can buy Eugene Porter all year. This is one of the brews that Revolution, our local craft beer powerhouse, always has available. But there’s no better time for a dark, creamy, delicious porter than mid-winter. It’s my personal pick for the best of the Chicago drinks for cold nights. Be warned, porters may not be for everyone.

This type of beer is just one shade above the intensity of a Guinness-style stout. So if you’ve tried a Guinness and found it “chewy” (as a friend of mine infamously said in college), then maybe skip this. But if you’re anything like me, then stock up now so you can make it through the hop-heavy beers of spring.

drinks for cold nights Chicago Eugene Porter Eugene V. Debs Socialist President poster
Who doesn’t want to drink a beer named after a perennial Socialist candidate for President?! Image via Wikimedia.

Can’t help but also point out that Eugene V. Debs, whom the beer is named after, is a local labor icon. He started the American Railway Union, which led to the infamous Pullman Strike. Not satisfied with merely upending the politics of robber barons, Debs went on to co-found the Wobblies. This internationalist workers’ movement wound up being best known for some members’ violent anarchist politics. So Debs struck out again and ran for President five times on the Socialist Party ticket. He was actually imprisoned when he was last on the ballot in 1920. You drink a ton of history in each sip!

#2. The Nitty Gritty or The Martinez at The Long Room

Chicago drinks for cold nights nitty gritty The Long Room
The Nitty Gritty at the Long Room is a coffee cocktail perfect for winter. Photo by J. Michael Bestul.

I reached out to my friend J. Michael Bestul for his take on the best drinks for cold nights. He’s a local cocktail connoisseur and a former member of the tasting room staff at North Shore Distillery. Safe to say that I trust any and all drink recommendations that he makes.

J. Michael recommended a visit to the Long Room, a tavern that’s been serving Ravenswood since 2000. Interestingly, they open at 8am every day except Sunday. Seems they operate more like a coffee shop and restaurant until 5pm. Then they switch over to being a more traditional corner tavern.

For the early arrivals, J. Michael vouches for The Nitty Gritty, a cold brew coffee cocktail. Loaded with Laird’s Apple Jack brandy and stout, it sounds like a great way to kick off a long weekend day of reading, writing, or playing games.

If you get there later, J. says to order The Martinez. Color me dubious, since it’s a gin cocktail and I hate gin. I suppose there’s a certain wintry feeling imparted by your whole mouth tasting like pine needles. I still call it gross But, if that’s your style, then gin mixed with vermouth, maraschino, and orange bitters does sound like the perfect antidote to a slate-grey Chicago winter.

#3. The Baby Darlin’ at Billy Sunday

drinks for cold nights baby darlin' billy sunday
Every cocktail at Billy Sunday is served in unique antique glassware. Photo by Morgan Lott.

This recommendation comes from our Private Tour Coordinator, Morgan Lott. She says that the Baby Darlin’ is her favorite local drink for cold nights because of its unique ingredient mix. It’s a rum cocktail, with vermouth, 1970’s Dom Bairo, burnt sugar bitters, and toasted orange. To quote her directly. “[The Baby Darlin’ has]…all the exoticism of a rum cocktail, all the coziness of burnt sugar and festive orange flavors. [B]ut it looks dark and mysterious.” I like the sound of that!

The bar where you can down the Baby Darlin’, Billy Sunday, is located right on Logan Square. Super-convenient for all of you Blue Line commuters! Billy Sunday himself was a professional baseball player turned evangelical preacher. He was a vocal proponent of Prohibition and conservative Christian values. It is perhaps a little ironic that a cocktail bar in liberal, youthful Logan Square (which you can tour with us) would be named after him. But, then again, I don’t think anyone has ever accused the residents of Logan Square of being ironic hipsters. 🙂

Know another spot with great drinks for cold nights? Email us or let us know through social media!

– Alex Bean, Content Manager and Tour Guide


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin

be a



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.”
Wade K


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.”
Katie K

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.”
Shelby F

Book a chicago event

Let’s Connect!