There's always cocktail season in the Windy City. And there are countless bars in Chicago to choose from. If you are on a vacation or a weekend trip and don't know where to go, picking a place can quickly become pretty overwhelming with so many cocktail venues in town.
- Best for Classic Cocktails: Billy Sunday
- Best for Whiskey: The Sixth
- Best Luxury: Violet Hour
- Best for Tiki Drinks: Three Dots and a Dash
- Best for Creative Cocktails: The Aviary
- Best Club-like: Arbella
- Best Speakeasy bar: Lazy Bird
To make your life a little easier, here are our favorite bars in Chicago. From classic to tropical to modern and fancy, we have a cocktail bar recommendation for everybody. And what they all have in common: each of these places will make you want to come back for more.
1. Billy Sunday
Billy Sunday Bar at Logan Square has long become an institution in Chicago's bar scene. Named after the evangelist Billy Sunday, the bar is a brilliant display of the owner's sense of humor. Why? Billy Sunday was a strong supporter of prohibition and is said to have played a significant role in passing the Eighteenth Amendment in 1919 - the ban on the manufacture, sale, and transport of alcoholic beverages.
The award-winning bar offers a mix of classic cocktails, adventurous modern creations, an impressive selection of vintage spirits, and a great passion for bitters and Italian Amari. The atmosphere is warm and welcoming, with a retro interior, paneled ceiling, and countless baroque picture frames.
Prices for cocktails mostly range between USD12 and USD15. But if you opt for one of their top-shelf drinks, your bill can show as much as USD65 per cocktail.
2. The Sixth
The Sixth bar is an elegant establishment in the charming area of Lincoln Square. It defines itself as somewhat of an upscale neighborhood bar, meaning it walks the fine line between the atmosphere of a sophisticated lounge and an approachable pub. And indeed, The Sixth has a very welcoming and warm atmosphere mixed with a modern, stylish interior.
The bar's name derived from a time in America's history when Whiskey production was so common that allegedly one in six men were involved in the business - may it be distilling, transportation, or grains and milling. And with the name already paying homage to Whiskey, it's no surprise that The Sixth features an extensive selection of this very spirit.
And besides the countless options for Scotch, Rye, and Bourbon, The Sixth is known for its craft cocktails and self-made, colorful specialty ice. Especially fun is the dealer's choice menu, where you pick spirit, flavor, and glassware. What you get is a delicious, beautifully presented surprise.
Prices for cocktails are USD14, and Dealer's Choice drinks are USD15.
3. The Violet Hour
If you are looking for something more quiet and exclusive, The Violet Hour is the place to go. It almost comes across like a lounge more than a cocktail bar with candlelight only and large, comfy chairs.
The no use of cell phone policy and a dress code that's strictly banning baseball caps might be a dealbreaker at times, but occasionally that's just the break one needs. Also, the choice of shaken and stirred cocktails is superb.
The name Violet Hour refers to the time of day when the sun starts to set and evening approaches. Poetically speaking, it's when wonders happen, and you can spot unicorns. And also, it is the cocktail hour. Labor stops, and it's time to relax. And people used to celebrate the end of a working day with a ritual, like having a drink. And poetry or not, at least the latter is still the case. And The Violet Hour is a fantastic cocktail bar to unwind.
Cocktails are USD16, except for the drinks in the luxury section, which clocks in at $40.
4. Three Dots and a Dash
Are you looking for tropical vibes in the Windy City? You can find them here, at Three Dots and a Dash. Probably one of the world's best Tiki Bars. This venue in a narrow backstreet in River North ticks all the boxes.
Tropical craft cocktails made with exotic fruits and spices, fresh, cold-pressed juices, homemade syrups, and the finest Rums come in phenomenal mugs in the shape of conch shells, sea urchins, mermaids, and the like. And also, the garnish lifts the drinks at Three Dots and a Dash to another level.
The interior combines the typical Tiki-style decor with modern, stylish elements. It is far from the slightly run-down-vibe tropical bar you may have experienced in other places. Three Dots and a Dash is all about high quality and creates a fabulous, fun, yet sophisticated atmosphere. For those who want to dive a bit deeper into the world of Rum, there's the Bamboo Room. It basically is a bar within a bar where you can get even more refined cocktail creations.
Drinks start from USD15. They also offer group drinks for up to 8 persons served in extra-large mugs in the shape of pirate ships, shells, etc.
5. The Aviary
When in Chicago, the Aviary is the place to go for special occasions as this is certainly no ordinary cocktail bar. And although that also reflects in the price tag, The Aviary is undoubtedly worth a visit.
You can expect the most unusual, astonishing, and progressive presentation and composition of drinks. Classic cocktails like an Old Fashioned come in a hollow ice ball you need to crack open with a rubber band. Other drinks contain tiny, spirit-filled bubbles that pop in your mouth or are served in impossible bottles featuring glass sailing ships inside.
Each and every cocktail is a piece of art - or probably of science would be the more precise description. And not only visually. Unexpected ingredients like truffle, caramelized onions, curry, or rare finds like aged Absinthe are starring on the drinks menu.
Upstairs the Aviary Bar is designed modern and lounge-like, while downstairs -the Office- is a small, intimate speakeasy-style bar with a fine selection of vintage spirits.
Cocktail prices are above average but reasonable for what you get and start at USD23. And I want to mention there is no dress code, but most people tend to dress up.
6. Arbella Chicago
Arbella Chicago is tasteful and stylish without being pretentious, also located in the River North neighborhood. The bar menu shows the outlines of a world map. And cocktails are arranged according to the areas that supplied the inspirations for the creations. Plus, there's a funny -and helpful- scale for you to check how much booze each drink contains.
They also have a special section where they celebrate the Old Fashioned by adding their globally-inspired twists to it. The selection includes, amongst various others, the Vietnam Rising, which features dragonfruit-lemongrass, or the Lago refined with habanero honey and elderflower.
Thursday to Saturday nights, you can enjoy live music events at Arbella Chicago, when they open their stage to DJ sets from local talents and international artists. The whole place radiates a pretty upbeat ambiance and is the perfect start for a night out.
Cocktails are USD16 each.
7. Lazy Bird
Lazy Bird unites the ambiance of a speak-easy-style cocktail bar with the vibes of a live music venue. The bar is located on the lower level of The Hoxton Hotel in the Fulton Market District. And they truly have an impressive selection of classics and modern cocktails on the menu. With more than 50 items on the list, they do not leave much to be desired. Bartenders at the Lazy Bird really pay attention to detail and deliver divine drinks.
Live music usually is on from Thursdays to Saturdays and features artists from all different genres. -From Jazz to Soul to Rock and Funk, there's something for everybody. Check out their monthly program to pick your favorite.
Also, you should know this is a walk-in bar only. So they don't take reservations. Especially on days with live performances, this can result in waiting times. So it is best to plan ahead a little and arrive early to avoid the queue.
Cocktails from the menu are USD16 and the dealer's choice drinks clock in at USD17.