Looking for the best Chicago bars? Well, you’re in the right place!
Chicago’s drinking scene is second to none, and the city’s bar offerings are as diverse and as unique as the Windy City itself!
Whether you’re looking for a nice place for a post-work beer with colleagues, or a funky hangout to do shots with your homies, Chi-town has some of the best drinking spots that’ll make you want to return over and over again.
Depending on your mood for the day, these best Chicago bars can cater to your drinking needs:
1. Three Dots and a Dash
Specialising in tropical cocktails made with seasonal fresh fruits, this intimate bar takes you on a walk across Columbia and Hawaii, with unique renditions made by expert mixologists.
This dimly lit, Polynesian-inspired space is fun, chill, and a great spot to enjoy good company.
Banana Daiquiri is one of the bar’s legacy drinks and has been on the menu since its inception. This is a frozen mishmash of three different rums along with coconut, lime, and fresh banana. It is well-rounded and delicious!
If you’re after something powerful, try the Jet Pilot. Again a mix of three different rums, this drink also has lime, Caribbean syrup, cinnamon, and bitters, which together bring about a powerful cocktail that is best enjoyed sipped slowly along with a side of their popular Coconut Shrimp.
The Painkiller combines a Caribbean rum blend with pineapple, tangerine, and coconut. It is as tiki-inspired as it gets!
What to order: Banana Daiquiri, Jet Pilot, Painkiller, Coconut Shrimp
Address: 435 N Clark Street, Chicago, IL 60654
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2. Kumiko
Located in Chicago’s West Loop is Kumiko, a Japanese dining bar, where food and drinks are adored equally.
The menu features extraordinary spirits and cocktails made with Japanese ingredients and techniques, and paired with great food, all enjoyed in an elegant, warm, and intimate setting.
To experience Kumiko to the fullest, you need to try the Component Flights. These are cocktails developed and served alongside Japanese sake that inspired the drinks.
Walk Softly is a cocktail that matches the elegance of the place without losing a beat. Made with rice vodka, sake, vermouth, and brut champagne, this drink is amazingly bright with just the right touch of bubbly.
Sea Flower is one of their highly popular cocktails. Blending gin, vermouth, sake, kabosu juice, and lime, this cocktail is zesty and refreshing.
For something provocative, try the New Wave. This unique creation brings back nostalgia to many, reminding you of the flavors of Japanese curry rice.
What to order: Component Flights, Walk Softly, Sea Flower, New Wave
Address: 630 W Lake Street, Chicago, IL 60661
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3. The Milk Room
Voted North America’s 50 Best Bars 2023, The Milk Room is located in the Chicago Athletic Association Hotel and is a micro bar with just eight seats, offering classic cocktails made with rare vintage spirits.
The stained glass doors, beamed ceiling, and vintage iron light fixtures give the room an old abbey vibe, and the cocktails are made by Chicago’s top and legendary bartenders.
Of course, what makes this bar stand out is the use of rare or vintage spirits to make amazing cocktails, which is also the reason why the menu here changes regularly, to introduce new vintage spirits.
On that note, a Milk Room classic is the Painkiller. This rum-centric drink has hot, spicy, and smooth Neisson L’Esprit rum as its base, which is combined with another 7-year-old single-cask rum, curacao liqueur, coconut, pineapple, and lime. It is certainly not for the faint-hearted but is equally refreshing.
Here, you could also try the spirits in their original form, and be mesmerised by their natural flavors and depth.
The Knob Creek Cherry Circle Room Single Barrel is a 10-year-old whiskey, aged beautifully to become a dark rich amber color and has a rich, full-bodied flavor.
If you can handle intense, Elijah Craig Milk Room Single Barrel Bourbon will knock your socks off! When bourbon is labelled “Barrel Proof”, you get to taste it in its purest form, and this 8-year-old drink is just outstanding.
What to order: Painkiller, Knob Creek Cherry Circle Room Single Barrel, Elijah Craig Milk Room Single Barrel
Address: 12 S Michigan Avenue, Chicago, IL 60603
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4. Long Room Chicago
Opened in 2000, the Long Room is a friendly neighborhood tavern featuring a timeless design, with no televisions, thereby offering a fully social atmosphere. With a long bar, cosy booths, a vintage photo booth, and also an enclosed beer garden, this watering hole is truly one of a kind.
Carbonated on draft, the Long Room Punch is fruity, fizzy, boozy, and absolutely refreshing.
Featuring mezcal, pineapple, jalapeno/celery juice, lime, and syrup, Long Room’s Green Limousine is yet another exhilarating preparation. This drink is so good and so popular that it was once a part of the bar’s cocktail-to-go program.
The Bumblebird is a delightful cocktail you’ll love sipping. This gin-based cocktail is fruity, herby, sweet, and so so good, you’d want it by the bucket!
What to order: Long Room Punch, Green Limousine, Bumblebird
Address: 1612 W Irving Park, Chicago, IL 60613
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5. The California Clipper
Humboldt Park’s very own tavern, The California Clipper is a historic neighbourhood bar serving seasonal cocktails and featuring live music. This landmark cocktail den has a classic bar vibe, featuring red leather booths and glowing red lights.
Matador is an enjoyable variation of the classic margarita. Made with tequila, spiced pineapple, and lime, the drink is perfectly balanced and also has a strong citrus flavor that gives it an edge.
Purple Martian has aged rum, pisco, concord grape, lime, and coconut; the flavor of the grape pairs well with the aged rum, giving the drink a profound flavor and also a beautiful colour.
How about some good ol’ cold beer? The award-winning Medalla Light is a crowd favorite, and there are over half a dozen of other varieties as well.
What to order: Matador, Purple Martian, Medalla Light
Address: 1002 N California Avenue, Chicago, IL 60622
6. Scofflaw
If we could mention one bar in Logan Square that is a balanced combination of excellent drinks, great food, and welcoming staff, it would be Scofflaw.
The menu here is hugely gin-focused, and the whole atmosphere gives you a Victorian era vibe, with exposed bricks, Edison bulbs, and tufted seating.
When you know that a cocktail bar’s menu is gin-focused, you should obviously start with Gin + Tonic. Here, they use Scofflaw’s very own Scofflaw Old Tom Gin, to be mixed with house tonic, juniper, lime, and rosemary. The rosemary adds a delicious savoury note to the drink, which is zesty, bright, and satisfying.
Swizzle #43 has sweet gwendoline gin, bittersweet liqueur, lemon, almond, and sherry. It is fragrant, slightly sweet, and gives a rounder mouthfeel.
They also have a serious and extensive collection of gin, and their Punch is quite popular too (ask for the day’s offering).
What to order: Gin + Tonic, Swizzle #43, Punch
Address: 3201 W Armitage Avenue, Chicago, IL 60647
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7. The Office
Located below The Aviary, The Office is a speakeasy-style bar, considered to be one of the best in Chi-town. The bar is tiny and intimate, with old-timey decor, and their drinks are made with extremely rare spirits by expert bartenders. The menu here is constantly changing and includes simple food options as well.
Cocktails at The Office are all about the classics. You can either go with pocket-friendly cocktails, or ultra-rare vintage spirits that cost at least a couple hundred dollars a glass.
One such delicious pocket-friendly drink is their Cognac. Made with a composition of bitters, liquor, smoked black pepper, and vanilla bean, this cocktail is beautifully rounded with hints of vanilla, spice, and bitterness.
The Rum cocktail with green tea, blood orange, and lime allures us with its dark colour, and you can taste every ingredient almost instantly when you take a sip of this full-bodied drink.
The classic Bobby Burns here is rich, smooth, slightly sweet, malty, and comes with a spicy twist at the end.
What to order: Cognac cocktail, Rum cocktail, Bobby Burns
Address: 955 W Fulton Market, Chicago, IL 60607
8. Nine Bar
As Chinatown’s first cocktail bar, Nine Bar is a speakeasy operating in the space that was once the dining room of Moon Palace – the neighbourhood’s favorite restaurant. The place is moody and dimly lit, with exposed bricks and upbeat music playing in the background (and DJs on the weekends) contributing to its lively vibe.
Start with the Nine Bar Mai Tai. This is a skillfully-executed variation of the classic tiki drink and has two different rums, citrus, and housemade almond cookie orgeat syrup. The syrup gives it a great nutty finish, and the drink is quite strong.
If you’re a fan of clarified milk punch, you’ll love Nine Bar’s Paradise Lost. The base of this cocktail is Thai coconut milk with novo fogo prata, pineapple, ube, and mango. You can taste the elevated tropical flavors in the drink, and the complex flavor profile makes you want to take it slowly to enjoy every bit.
How about something spicy, citrusy, and boozy? The Paper Dragon is a tequila-based drink spiced up by sichuan peppercorns, and refined with the addition of passionfruit and citrus.
What to order: Nine Bar Mai Tai, Paradise Lost, Paper Dragon
Address: 216 W Cermak Road, Chicago, IL 60616
9. The Green Mill
One of the oldest jazz hotspots in the country, Chicago’s Green Mill was a favorite hangout spot among celebrities and mobsters, from Charlie Chaplin to Al Capone. Great drinks, live jazz, and a humongous piece of Chicago’s history make this place is a standing relic of the bygone era.
Keep in mind that The Green Mill is not your contemporary cocktail bar and lounge; this is more cold beer and whiskey on the rocks kind of place.
If you like your beer crisp and smooth, you’ve got 3 Floyds Zombie Dust. A glass of this chilled beer could be the only breather you need after a zombie apocalypse (or a tiring day at work!). The lingering bitterness you experience after each sip is the best part.
For something strong, rich, and refined, go with the La Fin du Monde.
Dragon’s Milk Stout is warm, sweet, and caramel-y, with notes of coffee and chocolate.
A truly iconic Chicago drink would be Jeppson’s Malört. A shot of this full-bodied and aromatic bourbon could define your experience at The Green Mill.
What to order: 3 Floyds Zombie Dust, La Fin du Monde, Dragon’s Milk Stout, Jeppson’s Malört
Address: 4802 N Broadway, Chicago, IL 60640
10. The Violet Hour
Located in the heart of Wicker Park, The Violet Hour is a landmark craft cocktail destination in Chicago, serving artisanal cocktails with a rotating cocktail list and also a wide selection of spirits. The marble bar, candle-lit tables, and beautiful mural make this place ideal for casual date nights.
No, This is Patrick (yes, that’s the name of the drink!) is a unique blend of Control C Pisco, Malort, and a whole lot of fruity and fragrant additions, which together make this a fine, pure, and smooth drink. It is original and damn good!
The Luxury Old Fashioned features multiple award-winning TVH Russell’s Reserve Single Barrel bourbon whiskey and captivates us with its copper-red colour, and bold, spicy, and complex flavor.
The Violet Touch is a TVH classic; it is rich, and strong, and gets its savoury and spicy notes from the addition of tobacco bitters.
What to order: No, This is Patrick, Luxury Old Fashioned, The Violet Touch
Address: 1520 N Damen Avenue, Chicago, IL 60622
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That’s it for some of the best spots to go for a drink! Fancy rooftop drinking with a gorgeous view of the city? Chicago has some amazing rooftop bars with stunning views and creative concoctions.