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Trendy Bars Chicago Has to Offer

Welcome to the Windy City, where the nightlife is as diverse as the city. Chicago is home to a vibrant scene that attracts locals and visitors alike.

luxury interior at trendy bars in Chicago

Chicago has it all, craft cocktails, rooftop bars, and hidden speakeasies.

As a yearly visitor to Chicago, I have explored the city’s bars extensively and am excited to share my top picks for the best trendy bars in Chicago.

Check out my list of the best trendy 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 in Wicker Park is just minutes from the busy North Milwaukee Avenue shopping district.

It’s the perfect chic spot for a night out with friends or a first date you just have to impress.

This upscale and sophisticated bar showcases expertly crafted drinks from rare and vintage spirits.

Maria’s Packaged Goods and Community Bar

960 W 31st St, Chicago, IL 60608
Phone: (773) 890-0588
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Combining a trendy bar with a neighborhood liquor store, Maria’s Packaged Goods and Community Bar is one of the fun places to go out in Bridgeport.

It features retail space, food service, and a cozy and eclectic bar.

The bar is known for its extensive and vibrant selection of rare craft beers.


630 W Lake St, Chicago, IL 60661
Phone: (312) 285-2912
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Kumiko, an upscale and hip Japanese-inspired bar in the Union Park neighborhood, offers soft jazz nightly for dining or just to sit in and have drinks.

They serve a variety of cocktails, sake, and Japanese whisky to pair with their delicious dishes.

If you’re unsure what to choose, consider chef-selected cocktails.


5148 N Clark St, Chicago, IL 60640
Phone: (773) 334-9851
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The cozy Hopleaf, with its dark wood interior, is one of the best places to go out to if you’re a beer enthusiast, and it’s been serving Andersonville for 25 years.

The bar has an extensive beer selection, including a range of Belgian beers on tap and bottled, and a delicious food menu.

The Whistler

2421 N Milwaukee Ave, Chicago, IL 60647
Phone: (773) 227-3530
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If you’re looking for fun places to get drinks in Logan Square, consider The Whistler near the Logan Theatre.

This bar is cool and laid-back, focusing on live jazz and dance music, with no need to pay a cover charge.

Their custom cocktail list constantly changes, so check their social media for the latest offerings.

Three Dots and a Dash

435 N Clark St, Chicago, IL 60654
Phone: (312) 610-4220
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After strolling through the Chicago Riverwalk, venture a few more blocks, then down an alley to a hidden underground entrance.

Once you find it, you’ll find one of the best trendy bars in Chicago.

Indulge in one of the many handcrafted tropical tiki cocktails, and then buy a tiki mug to take home.

The Green Mill

4802 N Broadway, Chicago, IL 60640
Phone: (773) 878-5552
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The Green Mill is a famous jazz club that’s been serving the Uptown neighborhood of Chicago since 1907 and is still a cash-only establishment.

The divey atmosphere makes it a great place to bring music-loving friends.

Suitable for a dive bar, the Green Mill serves classic cocktails and a limited range of beers.

Nobody’s Darling

1744 W Balmoral Ave, Chicago, IL 60640
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Nobody’s Darling is a cozy, laid-back neighborhood bar in Andersonville.

After a day shopping in the Clark Street shopping district, stop in for a bite to eat, a drink, and occasionally to listen to live music.

This bar serves high-end spirits like Japanese whisky and elevated craft cocktails.


2771 N Lincoln Ave, Chicago, IL 60614
Phone: (773) 472-2771
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Delilah’s is a legendary punk rock dive bar in Chicago’s Lincoln Park neighborhood.

With its gritty but laidback atmosphere, it’s a fun place to get drinks with friends or go on a punk rock date.

The bar serves whiskey from 70 Scotch distilleries and craft beers, including many on draft.

Osito’s Tap

2553 S Ridgeway Ave, Chicago, IL 60623
Phone: (773) 277-8117
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In Chicago’s Little Village neighborhood, Osito’s Tap sits in a grey-storied building offering a wide selection of Mexican dishes with Latin accents, all in a cozy bar setting.

If you come just to drink, this no-frills spot offers a wide selection of premium Mexican spirits, tequila, beers, and classic cocktails.

Sportsman’s Club

948 N Western Ave, Chicago, IL 60622
Phone: (872) 206-8054
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If you’re looking for where to get a drink in the Ukrainian Village of Chicago, check out the unpretentious Sportsman’s Club.

It has a warming fireplace to relax by and plenty of space to include a few friends.

The Sportsman’s Club specializes in whiskeys but don’t miss out on their craft cocktails.

The Drifter

676-8 N Orleans St, Chicago, IL 60654
Phone: (312) 631-3887
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Speakeasies are very trendy right now, and The Drifter demonstrates why.

Hidden beneath the Green Door Tavern in the River North neighborhood, it offers an unforgettable evening with vintage decor, live music, and burlesque acts.

The Drifter has a rotating lineup of over 100 cocktails, including unusual experimental cocktails.

Kingston Mines

2548 N Halsted St, Chicago, IL 60614
Phone: (773) 477-4646
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Kingston Mines has been a world-renowned blues club in the Lincoln Park neighborhood since 1968.

If you love blues music, you must visit this club. The atmosphere is lively and energetic, with live blues music performances every night.

The bar serves classic cocktails and canned and bottled beers, including many prominent local brews.


3201 W Armitage Ave, Chicago, IL 60647
Phone: (773) 252-9700
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Scofflaw is a gin-centric cocktail bar in Logan Square, north of Wicker Park.

It has the qualities of a friendly local bar with vintage-inspired decor, cozy nooks, and upscale drink offerings.

This is a gin bar with nearly every gin made in Illinois. They also offer a small selection of beer and wine.

Cindy’s Rooftop

12 S Michigan Ave, Chicago, IL 60603
Phone: (312) 792-3502
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Cindy’s Rooftop is a chic rooftop bar in downtown Chicago at the top of the Chicago Athletic Association Hotel.

Here you’ll enjoy stunning views making it the perfect spot for brunch or a sophisticated night out.

The bar serves creative cocktails, including alcohol-free options and wines and beer.

The Aviary

955 W Fulton Market, Chicago, IL 60607
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The Aviary in Fulton Market is a high-end cocktail bar and lounge with swanky futuristic decor.

Intimate and chic, it’s a great choice to make a great first impression on a date or impress some foodie friends.

This sophisticated bar is known for its avant-garde cocktails with elaborate presentations using rare and unique spirits.

Old Town Ale House

219 W North Ave, Chicago, IL 60610
Phone: (312) 944-7020
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In the Old Town district, Old Town Ale House calls itself the best dive bar in Chicago.

A night here is like stepping back in time, with an old-school jukebox and stylings from the 1960s and 70s.

Old Town Ale House offers a variety of draft beers, including local and international specialty brands

Final Thoughts

Chicago is home to a vibrant bar scene, with trendy bars aplenty and a drinking spot to suit every taste.

Remember to check out some of Chicago’s other unique attractions, then share your experiences in the comments below.

What are your favorite trendy bars in Chicago? Let us know in the comments below!

Trendy Bars in Chicago

  1. The Violet Hour
  2. Maria’s Packaged Goods and Community Bar
  3. Kumiko
  4. Hopleaf
  5. The Whistler
  6. Three Dots and a Dash
  7. The Green Mill
  8. Nobody’s Darling
  9. Delilah’s
  10. Osito’s Tap
  11. Sportsman’s Club
  12. The Drifter
  13. Kingston Mines
  14. Scofflaw
  15. Cindy’s Rooftop
  16. The Aviary
  17. Old Town Ale House
Please drink responsibly, be fully accountable with your alcohol consumption, and show others respect.

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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