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20 Most Famous Cocktail Bars in Chicago to Try

Everyone loves to have a good brown-and-stirred drink when we land in a city of big shoulders. In Chicago, you will find the best wine houses and some of the best drinks in the entire country. Some world-class bartenders bless Chicago.

Cocktail bars Chicago has improved over time and now deliver some of the fine spirits combinations. If you don’t believe it, perhaps you should visit the best cocktail bars in Chicago by yourself.

However, you must know about the best spots even if you wish to taste their killer cocktails. Here, you will find some of the best cocktail bars in Chicago.

The Best Cocktail Bars Chicago

It would help if you enjoyed the last warm summer days by consuming signature cocktails at your nearest local bars in Chicago. You can taste whatever you wish in the Chicago cocktail bars. Searching for the best cocktail bar at night is also the best thing you can do in Chicago.

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Chicago features a wide range of bars. From rooftops to speakeasies, the West Loop to Little Village to Albany park, the local bars in this city are best for any event. They are filled with the finest and most friendly staff and the finest bar team in the world.

You will get hundreds of choices to choose a cocktail bar in Chicago. But the finest bar can only give you the pleasure you bidding goodbye to the summer season. In contrast, you must check the listed cocktail bars in Chicago, which are top raked in this city by locals and tourists.

1. The Matchbox Bar

This little cocktail bar is serving its best cocktails by the corner of Milwaukee, Ogden, and Chicago Avenues. Their specialty is the perfect lemon-lime margarita rimmed with powdered sugar. For more than 8 decades now, this bar has been slinging for the best city cocktails along with sidecars.

2. The Violet Hour

This cocktail bar is located in Damen Ave, Chicago. This bar serves the best artisanal cocktail. This cocktail bar also won the James Beard Award. The most attractive fact about this bar is its seasonal cocktail list, which has a wide selection of spirits.

3. Machine Engineered Dining And Drink

This restaurant also features one of the best cocktail bars in Chicago. It also serves a globally reputed latest American menu with a unique craft cocktail list. In addition, Machine also features a flower shop. This place could be a perfect place for your first date.

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It might look like an ordinary cocktail bar, but the menu of meals, cocktails, and bouquets is arranged for the best dining and drinking experience. The cocktail made here is made to exemplar by world-class bartenders. This is also why cocktail bars in Chicago are so famous. The cocktail menu is so perfect here that you can order anything.

4. Time Out Market Bar

Chicago city is filled with a bar on every floor of the Time Out Market. However, the main attracting bar of this building is located on the first floor. You will be fond of this unique bar when you first step in. This bar is also the largest in the entire building of Time Out Market Bar.

You will see fun flavors on every floor corner when you enter this building. The cocktails are specially curated by beverage director Jonathan Kahn. He incorporates the local spirits from the makers of CH Distiller and Apologue. The menu of the cocktail is rounded here by the director with some top-rated wine. This bar also features some Chicago-made brews according to the preferences of Metropolitan Brewing, Off Color Brewing, and Moody Tongue.

5. Osito’s Tap

This cocktail bar is located in the back of Moreno’s Liquors and features some rare tequila, which is very hard to find in other bars in the city. Osito’s Tap not only sells rare spirits, but it is also selling mezcal in Little Village for more than 40 years now.

The cocktails made here are from selected ingredients, including ancho chile and an impressive draft beer. When you step into this bar, its interior décor will take you back to the bar’s historic interior. You can even help yourself by grabbing a seat on the patio and soaking yourself in the sunshine with their rare spirits.

6. Three Dots And A Dash

This cocktail bar is famous for its unique and special menu. It is blended with tropical flowers, fresh herbs, citrus, and colorful bendy straws. The Bamboo room of this bar features exquisite tiki cocktails crafted from fresh pressed juices and house-made syrups. The arsenal of this place has been taken to the next level.

If you are having a fast time in Three Dots And A Dash Bar, you should start with the namesake cocktail. It blends allspice, orange, lime, falernum, and finest rums. It is fully packed with cream cheese and some tender crab meat hunks. If you feel comfortable with the finest cocktails, you can order the king crab rangoons.

7. La Josie

The La Josie bar is located in the West Loop of Chicago city. This bar is a family-owned Mexican spot that can offer you all sorts of Jalisco-inspired foods, some colorful ceviches, and hand-pressed tacos. Though the food here is much more delicious and known all over the city, this place is more famous for its cocktail lists.

 8. Bordel

Bordel bar is located in Wicker Park. Head upstairs to Mama Delia behind a secret door to find this bar. This bar is not only best for its cocktail list but also features nightly live entertainment, giving a perfect vibe for its vintage spirits.

This place is a fun place for whiskey lovers. You can have this ancient forthy Lost in Paradise cocktail, which will take you back to the last golden age of cocktails. It is made from Scotch, lemon, demerara, and spiced pear brandy.

9. The Aviary

This is a famous cocktail bar located in the Fulton Market in Chicago. This bar will offer you creative cocktails and many other delicious foods. The beverage director Micah Melton prepare the cocktails. The cocktails receive the same innovative treatment as the food at the Next or Alinea.

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The Aviary is loved any locals and also by tourists. The creative cocktails here will leave you amazed. Their delicious taste and the perfect blend are the best you will ever have. However, you should expect to drink cocktails like the Ford’s Model Tea Party. Once you visit this bar and taste its cocktail, you will realize its worth. You can also taste other spirits.

10. The Berkshire Room

This bar is located in the River North of Chicago, and the bar typically seems much bigger than it is. However, the scrapped ceiling and the checkered floor with Alice in Wonderland is the special attraction of its interior décor. Besides this décor and intimate setting, The Berkshire Room is much more comfortable. Even the cocktails available here are much tastier and can defy your expectations.

Though you will find some of the best collections of provincial spirits, you can create your own special drink, which is Dealer’s Choice. In this special cocktail, you will be asked to pick up a spirit from two given options. Besides this, you will have to pick a flavor profile and glassware, which can be smoky, spicy, or Collins glass. This is the best service that you will get in Chicago cocktail bars. The Berkshire Room will create a special cocktail only for you.

 11. Drumbar

The Drumbar can be found in Streetsville. This is a stunning place to spend your evening sipping on some fine cocktails from the city. Other than this, some visitors consider this place ideal for their unfettered Instagram photos. You will be amazed by the cocktail list of this bar. Drumbar is known to make the finest cocktails in the town. The best of the house is the seasonal cocktail and their drinking session on their couch.

You can choose to form the special cocktail list of Drumbar, which also features the famous Nouveau Negroni. You can enjoy these drinks in a drinking hub on the Raffaello Hotel on the 18th floor.

12. The Whistler

This is another famous bar in the town, located in Logan Square. But since the golden era, The Whistler has drawn huge crowds to its bar. The craze for this bar is solely due to the efforts of the 3½ years of Pail McGee. He spent all these days making the perfect cocktail. Even after this death, the bar still runs at full pace with uncountable visitors worldwide.

This place is not only an antique place that will give you thrills, but it also offers music and affordable drinks. The price of drinks here ranges from $8 to $13. Also, The Whistler once supported the craft-cocktail movement in Chicago. Besides drinking famous cocktails from this place, you should also check out rotating art installations, film screenings, andmovieokie.”

13. Bar Sotano

The Bar Sotano can be found in the River North of Chicago. This subterranean cocktail den holds some top-notch cocktails from Rick Bayless’s daughter Lanie Bayless. They use a wide range of ingredients to blend their special cocktail. Bar Sotano uses Mexican medicinal herbs, lime mango, chamoy, and some splash of Topo Chico.

Surprisingly the food here is so good that you can never go wrong with it. You will get different types of snacks, ranging from ceviches to tacos. The Bar Sotano has the best snacks with its famous cocktails.

14. Moneygun

This cocktail bar in West Loop sells classic cocktails and 90s hip-hop. These two things will take you back to the old days, and this can be your dream bar in Chicago. Though Moneygun has a small and dark space, it features all originals, ranging from the mojitos to sidecars and sazeracs. Their specialty is the “Monthlygun” selections.

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Each sip you drink here has the perfected recipe, and the quality is top-notch, often made with house-made ingredients. You can enjoy the bar’s classical drinks and the snacks loaded with waffle fries, seasonal empanadas, and chocolate chip cookies.

15. Punch House

The Punch House is located on the Lower West Side of the town, below Dusek’s Board and beer. It is a ‘70s-themed dark bar. The interior is decorated with a fish tank and wood paneling, and you will also find a huge fish on the wall. This bar might bring some memories of your grandparent’s basement. The name punch is the most beautiful thing about this place. In the Punch House, you can order cocktails by glass, carafe, or bowl.

It doesn’t matter if you opt for big or small, but you will experience the vibe of the back bar at the Punch House. If you are looking for some good drinks to start with at the Punch House, you go with the Space Juice for Jered. It is a special blend of tequila, lime, grapefruit, black pepper, sparkling wine, and some sage. After a few glasses, you can opt for the piano bar Tack Room if you feel comfortable with this cocktail and the place’s vibe.

 16. Billy Sunday

This classic cocktail bar is located in Logan Square, the town. The beverage director of Billy Sunday manages the menu of the original classic cocktails and all the twists on the classic Amari. Billy Sunday might be a bar, but the food found here is a worthy companion to your classic cocktails. You must not miss any of the snacks from this place.

17. Nobody’s Darling

This cocktail bar in Andersonville is a black-women-owned bar that sells classic drinks with a sleek and intimating atmosphere. You will find the martinis, mimosas, and sangrias here, directed by the owners of this place, Renauda Riddle and Angela Barnes. The cocktails are blended with lychee, basic blueberry syrup, and mango.

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The famous Alice Walker poem inspires this place name. At Nobody’s Darling, you will notice that the cocktails here fall into different categories. Boozy Darlings, Darling Cocktails, categorize them, and Darling You’re Drunk. It depends upon the amount of alcohol content.

18. Sportsman’s Club

This bar on Western Ave is the greatest industry bar in the town. You can taste its classical cocktails with your friends on Saturday nights. The Sportsman Club is a unique bar for its amaro machine. This club has a daily changing blackboard menu with an outstanding design. The interior of this place is decorated with chess. The tables here are designed with checkers, and it also features a large and beautiful backyard.

19. The Sixth

The Sixth bar is located in Lincolns Square. When you take some sips of cocktails from The Sixth, you may think you are currently in the Downtown lounge. If you suffer from a lack of assertion, this place will quickly snap you back to reality. In this bar, you will find all types of spirits-mixing wizardry. The cocktails here are made with special ingredients. It includes bourbon, Dark Matter coffee, a dram of chocolate, and pipe tobacco.

20. Cindy’s Rooftop

The Cindy’s Rooftop bar is located in The Loop, high above Michigan Avenue at the Chicago Athletic Association hotel. If you want to take your friends on a city tour, then this rooftop bar is the perfect place. This can be your dream place to flaunt the beautiful Lake Michigan.

Cindy’s Rooftop bar is even famous for serving some top-class cocktails. To taste their cocktail, you must take the Tierra Roja, single-blended with Mexican rum, passion fruit, lime, and mezcal.


There are hundreds of bars to hop in with your friends. The bars in Chicago serve the best cocktail in entire Illinois. If you plan to visit the best cocktail bar in Chicago, you must consider the bars mentioned above. These are the best bars that you will ever encounter in Chicago. However there are even many other bars but if you wish to taste the vintage and best cocktails, check out these bars.

In the cocktails bars Chicago, you will find the best craft cocktails, a milk room for whiskey lovers, a rooftop bar, some signature cocktails of extensive selection, and some unique drinking destinations with a dance floor.

Also read: Best Rooftop Restaurants Los Angeles.

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Last Updated on September 30, 2023 by Shubham95c

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