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Most Popular Cocktail Bars in the Chicago Area

Are you traveling to Windy City soon? I’ve got you covered with a list of the best cocktail bars in Chicago.

people drinking cocktails in one of chicago's best cocktail bars

Chicago has something for everyone, whether you love a classic cocktail, an innovative drink, or something non-alcoholic. Visit a charming speakeasy, a classy hotel lounge, or a divey local bar.

Read on to learn more about the top places to grab a cocktail in Chicago, Illinois. Check out my list of the best cocktail bars in Chicago below!

The Violet Hour

1520 N Damen Ave, Chicago, IL 60622
Phone: (773) 252-1500
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The Violet Hour is an upscale bar with cocktails in Wicker Park. It’s just off W North Ave, near the local community garden, and you can relax in the swanky bar with a handcrafted drink.

I suggest trying a Ruby in the Sky shaken cocktail or the Saz-Daddy cinnamon apple brandy.

Three Dots and a Dash

435 N Clark St, Chicago, IL 60654
Phone: (312) 610-4220
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Head over to Three Dots and a Dash in the River North area. It’s a Polynesian cocktail bar with retro vibes and a tropical theme.

This hip joint features fruity cocktails, fresh pressed juice, and authentic aged rums. I like the Caribbean rum Painkiller cocktail with tangerine, pineapple, and coconut.

The Aviary

955 W Fulton Market, Chicago, IL 60607
Phone: (312) 226-0868
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The Aviary is an upscale cocktail lounge in Fulton Market. It’s hip and trendy, with creative drinks for everyone in your crew.

Try my favorite focaccia bread with whipped ricotta cheese and olive oil, and pair your meal with a Cody Road rye Red Hook with orange bitters and maraschino.


630 W Lake St, Chicago, IL 60661
Phone: (312) 285-2912
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I like to visit Kumiko when I’m in Chicago. It’s a Japanese cocktail bar on W Lake Street, not far from the Chicago River.

The spot has hip vibes, and you can try creative Japanese plates with your favorite cocktail. Check out the Sea Flower gin or Last Rose cocktail with elderflower.

Billy Sunday

3143 W Logan Blvd, Chicago, IL 60647
Phone: (773) 661-2485
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Billy Sunday is an award-winning cocktail bar in Logan Square Park. It’s across the street from the Illinois Centennial Monument, and the bar has a vintage vibe and gourmet menu.

I like to order a Normandy draft cocktail with hints of lemon verbena. You may also enjoy the Sunday Candy cocktail with coffee liqueur.


4716 N Kedzie Ave, Chicago, IL 60625
Phone: (773) 754-0129
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Head to East Albany Park to visit Bokeh, a cozy cocktail lounge with light fare and creative drinks. There’s a regular in-house DJ, and the atmosphere is relaxing and casual.

It’s ideal for an evening with a group of friends. I like the bittersweet house Bokeh drink with citrus. The Turkish Delight with rum is also fantastic.


12 W Elm St, Chicago, IL 60610
Phone: (312) 725-0732
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Visit the trendy Cuban bar for a vintage art deco vibe. The retro interior of the circa 1927 building gives the bar a Prohibition-era feel.

Sparrow is in the Near North Side district, near Oak Street Beach. I like to order a Grasshopper when I’m at Sparrow.

Matchbox Bar

770 N Milwaukee Ave, Chicago, IL 60642
Phone: (312) 666-9292
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Matchbox Bar is a tiny cocktail bar in the River West district. Visit early in the evening, as this spot tends to get busy!

This hip bar has been around for over 75 years and claims the title of Chicago’s oldest. I like to grab a seat on the outdoor patio and sip a Cosmopolitan or Pinot Rose wine.

The Victor Bar

4011 N Damen Ave, Chicago, IL 60618
Phone: (773) 360-7049
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I always visit The Victor Bar when I’m in the city. It’s on N Damen Ave in north Chicago and has a modern feel.

This chic bar features some of my favorite drinks like the Scotty Doesn’t Know scotch and local beers like the Palm Shade IPA and Helles Lager.

The Sixth

2202 W Lawrence Ave, Chicago, IL 60625
Phone: (773) 433-5959
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The Sixth is a trendy cocktail bar on W Lawrence Ave in the Ravenswood district. It’s a modern spot with specialty ice, seasonal ingredients, and top-tier cocktails.

Try the Sherry Baby cocktail with spiced pear, or check out the Hidden Gem rye and vermouth with hibiscus and hints of citrus.

Vol. 39

39 S La Salle St #200, Chicago, IL 60603
Phone: (312) 604-9909
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Don’t leave Chicago without visiting Vol. 39 in the downtown area. It’s near all the top sights, including the Art Institute of Chicago and Willis Tower.

This upscale cocktail lounge is in the lobby of the Kimpton Gray Hotel. Try a Chaos Warp tequila or a relaxing Hot Spiced Cider.


3201 W Armitage Ave, Chicago, IL 60647
Phone: (773) 252-9700
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Are you a fan of gin cocktails? Scofflaw in Logan Square is a perfect choice for you.

The trendy late-night cocktail bar features global cuisine and chic drinks like the Broker’s London Dry Shipwrecker, the Rye Swizzle, and the Past Life with Letherbee gin. Don’t forget to try Korean rice cakes!


112 W Grand Ave, Chicago, IL 60654
Phone: (312) 846-6654
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Arbella Chicago is a hip cocktail lounge and loft on W Grand Ave, near the iconic Merchandise Mart in the River North district. It’s a trendy, modern spot with small bites and housemade cocktails.

I suggest trying a tequila lime seltzer cocktail. The menu changes seasonally, so call ahead to see what’s on.


660 W Lake St, Chicago, IL 60661
Phone: (312) 600-0600
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Visit Moneygun, a no-nonsense cocktail and small plates bar in the West Loop Gate area. It features New American cuisine, and the place feels hip yet relaxed.

I like to grab a Cosmopolitan vodka with cranberry cordial or a Bee’s Knees cocktail with gin, honey, and lemon when I visit Moneygun.

The Whistler

2421 N Milwaukee Ave, Chicago, IL 60647
Phone: (773) 227-3530
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You have to visit The Whistler in northwest Chicago. It’s an ideal place for music lovers, and you can hear live DJs or local bands perform at the cocktail bar.

The vibe is relaxed, and the menu features cocktails like the Edge of Tomorrow and Old Faithful.

The Drifter

676-8 N Orleans St, Chicago, IL 60654
Phone: (312) 631-3887
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Are you looking for a speakeasy in Chicago? Look no further. The Drifter is the top speakeasy in Windy City, and the place has a vintage, chic vibe.

It’s an upscale basement bar in the River North district, and you can order cocktails based on tarot cards and movie references. Try the Ace pear cider if you get a chance.

Weegee’s Lounge

3659 W Armitage Ave, Chicago, IL 60647
Phone: (312) 278-3248
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Weegee’s Lounge is a spot in Logan Square you won’t want to miss. It’s a 1940s-themed pub with a cocktail bar, shuffleboard table, and craft beers.

The place is cozy and ideal for a romantic evening or a small group of friends. Try the classic Manhattan or Corpse Reviver cocktail.

Lazy Bird

200 N Green St, Chicago, IL 60607
Phone: (312) 761-1799
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I like to visit Lazy Bird, a cellar-level cocktail bar in the famous Hoxton hotel. It has a chic yet relaxed vibe with unique handcrafted cocktails and a small snack menu.

Head to the Fulton Market area and visit this trendy joint. I recommend the Espresso Martini for an extra kick.

Bordel | Cabaret & Cocktail Bar

1721 W Division St, Chicago, IL 60622
Phone: (312) 487-1236
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Check out Bordel Cabaret & Cocktail Bar before you leave Chicago. It’s on West Division Street and features lots of live performances.

This upscale cocktail bar is in the East Village and is among my favorite in the city. I suggest ordering a daiquiri or a white banana negroni.

The Bamboo Room at Three Dots and a Dash

435 N Clark St, Chicago, IL 60654
Phone: (312) 610-4220
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Drive to the River North area and visit The Bamboo Room, a tropical cocktail lounge not far from the river. It’s a perfect place to visit when you’re in downtown Chicago.

Sample the Hot Buttered Rum drink, or check out an Isle of Mango cocktail with blended whiskey and vanilla.

King of Cups

2238 N Lincoln Ave, Chicago, IL 60614
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King of Cups is a classy cocktail bar with an extensive menu. The goth environment is dimly lit and features chandeliers and funky decor.

Hit up King of Cups after visiting the iconic Oz Park in Chicago’s North District. I recommend drinking an Absolute Rule gin at the cocktail lounge.

Love Street

1325 W Wrightwood Ave, Chicago, IL 60614
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Love Street is a low-key cocktail bar in the Sheffield and DePaul area of Chicago. It’s not far from Wrightwood Park and is ideal for a chill afternoon with friends or family.

I like to order a vodka lemonade usually. Or, try a local Helles Lager draft beer.

Elixir Lounge

3452 N Halsted St, Chicago, IL 60657
Phone: (773) 975-9244
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Elixer Lounge is a cocktail bar that has something for everyone. The environment is casual, and the bartenders serve classic and innovative cocktails in Chicago’s Northalsted district.

Try a Dark and Stormy rum cocktail, or check out a shaken drink. I like the Mint Julep with bourbon and simple syrup.

The Green Mill

4802 N Broadway, Chicago, IL 60640
Phone: (773) 878-5552
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The Green Mill is the best cocktail bar in Chicago for jazz lovers. It’s a jazz club with live shows and plenty of drinks.

The spot is north of the Uptown district, near the Riviera Theatre. Sample a chardonnay, red wine, or draft beer. I like the Mendoza from Argentina.

Spilt Milk

2758 W Fullerton Ave, Chicago, IL 60647
Phone: (773) 413-8440
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Spilt Milk is a 1920s-themed cocktail bar north of Palmer Square on W Fullerton Ave. I like to visit and enjoy the old-school vibes and classic cocktail mixes.

I recommend visiting from 4-7 on weekdays for happy hour. Try the Itsy Bitsy Cider cocktail with spiced maple syrup and lime.

Final Thoughts

The Windy City is one of the best places for cocktail bars. Chicago has trendy lounges, Prohibition-style bars, and casual outdoor patios.

Visit Chicago’s cocktail bars, and you won’t be disappointed! If you have any suggestions about the best cocktail bars in Chicago, leave us a comment below.

Best Cocktail Bars in Chicago, Illinois

  1. The Violet Hour
  2. Three Dots and a Dash
  3. The Aviary
  4. Kumiko
  5. Billy Sunday
  6. Bokeh
  7. Sparrow
  8. Matchbox Bar
  9. The Victor Bar
  10. The Sixth
  11. Vol. 39
  12. Scofflaw
  13. Arbella
  14. Moneygun
  15. The Whistler
  16. The Drifter
  17. Weegee’s Lounge
  18. Lazy Bird
  19. Bordel | Cabaret & Cocktail Bar
  20. The Bamboo Room at Three Dots and a Dash
  21. King of Cups
  22. Love Street
  23. Elixir Lounge
  24. The Green Mill
  25. Spilt Milk

Written by Rocco

Rocco is a Florida State University alumnus with years of bartending and hospitality experience. From slinging hundreds of vodka sodas a night in jam-packed college bars to serving carefully crafted cocktails in upscale restaurants, there’s not much he hasn’t done behind a bar. Now, Rocco shares his knowledge and passion for all things alcohol-related here on My Bartender for bibulous readers everywhere to enjoy.

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