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7 Most Expensive Bars in Chicago You Can Go To

In Chicago, revelers can sip their favorite drinks in many upscale establishments.

cocktail drinks at most expensive bars in Chicago

The locals demand quality services, which can, understandably, only come at an above-average price.

I explored this part of the Midwest, sifting through cocktail lounges, alehouses, and speakeasy bars.

Check out my list of the most expensive bars in Chicago below!

Three Dots and a Dash

435 N Clark St, Chicago, IL 60654
Phone: (312) 610-4220
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The bar by the exciting name, Three Dots, and a Dash, has a simple vibe that could make you mistake it for an average bar.

But as they say, the proof is in the pudding. In this case, the proof is in the drinks served at the bar.

This expensive bar has the widest selection of drinks I’ve come across and boasts professional staff who can make you any cocktail you like; they welcome the challenge!

The Up Room

2018 W North Ave, Chicago, IL 60647
Phone: (872) 315-3060
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Cool and presentable are the first impressions I got at The Up Room. It’s a tiny bar on the 13th floor of the infamous Robey Hotel.

The views are breathtaking, and the drinks flow to infinity. Come prepared for your eyes and palates to be awed.

You may have to chuck slightly more to have your favorite cocktail, but the experience will be well worth it.

The Berkshire Room

15 E Ohio St, Chicago, IL 60611
Phone: 312-894-0945
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Chicago has quite a selective crowd of drinkers.

What makes The Berkshire Room stand out and ever busy is the excellent service you’re guaranteed to get.

Not sure what you want to take? The bartenders will gladly swoop in and make you a drink you’ll never forget.

All you’ve got to do is pick a glass.

The Signature Room at the 95th®

875 N Michigan Ave, Chicago, IL 60611
Phone: (312) 787-9596
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This posh, elegant joint that’s sure to leave its mark on your memory is as unique as every handwritten signature.

Here, you pay not only for great drinks but for convenience.

During my visit, I expected to wait in line for a long but was seated within five minutes.

Background music was soft and classy, and the surroundings were flawless, as you’d expect!

The Aviary

955 W Fulton Market, Chicago, IL 60607
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The Aviary bar stands out in terms of creativity. It’s an elegant and intimate spot that makes you feel like a million bucks.

Yes, you’ll probably come across many celebs and athletes here; a hint at the unparalleled services, food, and drinks you’ll get here.

Le Bar Chicago

20 E Chestnut St, Chicago, IL 60611
Phone: (312) 324-4000
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If you want to keep up with the newest trends in Chicago, Le Bar Chicago is the place to be.

I started simply by ordering a margarita and later asked for a Veuve Cliquot, which I could get by the glass.

To say I was impressed is an understatement!

ROOF on theWit

201 N State St 27th Floor, Chicago, IL 60601
Phone: (312) 239-9502
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If you want a rare treat of the Chicago skyline, Roof On the Wit is the place to be.

This well-reviewed bar serves hand-crafted drinks and delicious meals that will surpass your standards.

The bar has an unintimidating vibe and is best for anyone looking for nice place for nighttime fun.

There it is; you’ve been let in on well-kept secrets of some of the most expensive bars in Chicago that are well worth your while.

Do you know of other bars we could add to this list? Comment down below.

Please drink responsibly, be fully accountable with your alcohol consumption, and show others respect.

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