Where To Go When You’re In The Mood For An Old Fashioned11 bars and restaurants for when you don’t just want any drink—you want an Old Fashioned.
This is not a guide to the best Old Fashioneds in Chicago. This is a guide to the best places for when your shirt is tucked in, and you're feeling dignified. For when all you want to do is stare contemplatively into a fireplace and think about your life in short, Hemingway-ian sentences. When the only thing to match your feeling of refinement is a timeless drink of spirit, bitters, and sugar.
Drinking an Old Fashioned is a mood. It doesn’t matter whether it’s made with whiskey, bourbon, or even tequila. What matters is the setting in which you drink it. And, of course, it has to taste great too. These are the best bars and restaurants for when you’re in the mood for an Old Fashioned.
“No baseball caps, no light beer, no Jager-bombs or drink bombs of any kind.” These are just a few of the house rules that set The Violet Hour in Wicker Park apart as a classy, no-bullshit cocktail bar. And even though it opened in 2007, it remains one of the best places to go when you want to feel like the epitome of sophistication. The dark space is illuminated with flickering candlelight, and has floor-to-ceiling velvet curtains and high-backed leather chairs begging to have a first edition of Ulysses resting on one of the side tables. And there’s no better drink to go along with this cultured aura than a classic Old Fashioned, or their tequila-based Oaxacan version, that’s a perfect balance of sweet and smoky.
Union is the neighborhood bar/restaurant that you want to have right around the corner during Chicago’s seemingly endless winter. They have a great burger, fantastic drinks, and warm, inviting energy even when it’s packed. Whether you’re sitting in a booth, communal table, or drinking at the bar, this is a place to get lost in thought while nursing either of their four fantastic Old Fashioned options, made with either whiskey, bourbon, or rum. The warmth of its amber lighting mixed with its wooden and brick interior make it cozy enough to melt away any icicles that might have formed around your face on the walk there.
Everything at Kumiko in the West Loop is about the details. From menus that look like art zines to the way staff describes flavor profiles like they’re whispering sweet cocktail nothings, this is one of the best bars in the city. It’s particularly great for a quiet date night, where you can stare deeply into your partner’s eyes while swirling the ice cube in your rocks glass before mentioning that you forgot to transfer the laundry. Their standard Old Fashioned is great, with just enough booziness from the mix of whiskey and shoshu, all while a hint of sherry adds a little bit of lightness. And if you want to eat while having this tête-à-tête, they also have some delicious katsu sandwiches.
Where To Go On A Date Right Now In Chicago
Sometimes you just want to drink an Old Fashioned alone, perhaps while pretending to be a worldly traveler passing through a small town. One of the best places to channel this main character energy is Longman and Eagle in Logan Square. This restaurant’s mahogany interior is frequently filled with loud music and even louder people having dinner, but there are often one or two spots at the bar open. Here you can blend in with the crowd, all while shrouding yourself in mystery and intrigue. And if you actually are a mysterious traveler “just passing through,” they have six rooms above the restaurant if you need a place to stay the night.
With its cozy narrow space, dim lighting, and exposed brick, Victor Bar reminds us of a speakeasy minus a secret entrance you’ll walk by five times before finding. This North Center bar embodies brooding charm—candlelight, friendly crowd, and you'll never find yourself competing with the people around you to be heard. It's perfect for sitting with a friend and waving around a rocks glass while unpacking the existential questions posed by The Metamorphosis. Be sure to jot down your thoughts in a tiny pocket Moleskine notebook.
Regardless of the spirit or the bitters, the best flavor enhancer for an Old Fashioned is some jazz. And one of our favorite places to go for classic cocktails and live music is Lazy Bird in the West Loop. This dimly lit, 1940s-meets-modernist bar is located in the basement of the Hoxton, and has plenty of soft couches and chairs for you to sink into while listening to some velvety crooning. And though they have an exhaustive cocktail list, everyone knows that the ideal drink to accompany Billie Holiday is a classic Old Fashioned.
The Chicago Bar Hit List: Where To Drink Right Now
Dim and cozy, this relaxed speakeasy inside of Pilsen Yards is discrete, perfect for low-key drinks or dabbling in light corporate espionage. Here, you can meet up with your contact and discuss trade secrets while sipping on a fantastic cocktail. They have a great classic version, but for something a little more interesting, their Whimsy Old Fashioned (made with smoked oleo tea and truffle bitters) has a nice balance of sweetness and funk. Just be aware that the tables are fairly close together and you never know which of your neighbors might be listening in.
With its vintage interior, ornate fireplace, and upholstered leather booths, this Lincoln Park tavern from the Au Cheval team looks like a Prohibition-era clubhouse. The best cocktail to romanticize illegal drinking is an Old Fashioned, and here you can enjoy the 1920s charm without worrying if your bourbon was made in a bathtub. Pair it with one of their excellent rotating pot pies.
A night out at this busy rooftop bar in the Loop means drinks, crowds, and one of the best views of the city. It also often comes with an existential inner dialogue. Maybe it’s the hour-long wait for the elevator that has us contemplating the fleetingness of life. Perhaps it has to do with the feeling of insignificance we experience on the balcony, with the night sky and high rises towering above us. Or maybe it’s because every time we come here we wonder why we went through all this effort just to be surrounded by a bunch of tourists. Either way, existential thoughts go hand in hand with Old Fashioneds, and luckily, theirs is pretty good.
The Best Chicago Rooftops For Eating & Drinking
At Bronzeville Winery, drinking an Old Fashioned isn’t about rigid formality. "Classy yet playful" is the best way to describe both this restaurant’s atmosphere and their take on the classic drink. The Uncle Yams Old Fashioned made with sweet potato syrup and garnished with roasted marshmallows is sweet and whimsical, but still has the bold flavor of a classic Old Fashioned. This upscale place has a sleek interior and artfully plated food, but their DJ spinning funk jams is a good reminder to relax, have fun, and not worry if you have a marshmallow all over your face.
At one point, whiskey, sugar, and bitters went out of style in favor of gin or vodka-based drinks—which led to the term “Old Fashioned.” And at this mid-century-looking cocktail lounge in The Acme Hotel, you can show everyone what a rebellious, liquor-drinking trailblazer you are. By ordering the Dealer’s Choice, you can tell the staff what spirit you want, the flavor profile, and the glass you want it in if you think rocks glasses are so 1880s. Rum or whiskey. Fruity or earthy. The possibilities are endless—go forth and be a fearless pioneer.