The Official Chicago Bar Bucket List | UrbanMatter
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The Official Chicago Bar Bucket List

Chicago Bar Bucket List

The Official Chicago Bar Bucket List

Bucket lists—we all have ’em. And if you’re anything like me and love exploring Chicago’s bars, these are just a few you absolutely must add to yours.

Here’s UrbanMatter’s official Chicago Bar Bucket List.

How many can you check off?



Chicago Bar Bucketlist

Photo Credit: SafeHouse Instagram

60 East Ontario, River North

Get your spy on at this espionage-themed bar in the Near North Side. You don’t want to miss out on all the surprises that comes with a visit to this unique Chicago bar. Hit up the many bars that are incorporated in the venue, and take the secret exit to leave.


The Office

Chicago Bar Bucket List

Photo Credit: The Pouring Tales

955 West Fulton Market

Located beneath The Aviary, this speakeasy serves classically inspired cocktails. You wouldn’t know it was there unless you were looking for it, but once you’re in it’s absolutely breathtaking. Ask for the “dealer’s choice,” and the bartender will ask you questions to find out what your tastes are. Then he will make something based exactly on the taste you described. Top off the night with a handwritten check written in calligraphy.


The Drifter

Chicago Bar Bucket List

Photo Credit: The Drifter Instagram

676-8 North Orleans, River North

Another Chicago speakeasy, The Drifter is located under Green Door Tavern. Once you get down the stairs, look for the doorknob hidden in the bookcase. On top of that, enjoy their live entertainment that might include burlesque or comedy. Oh, and the drink menu is printed on tarot cards too.


Three Dots and a Dash

435 North Clark, River North

This underground tiki bar is definitely one to add to the bucket list. That is, if you haven’t yet already. They serve a variety of tiki drinks, including some extra fancy flaming options. The bar spans 200-plus rum options in a Polynesian island setting. Order a large drink for a couple or group, or one for yourself.  Either way, you can be sure to enjoy the unique presentation.


Headquarters Beercade

Bar Bucket List

Photo Credit: HQ Beercade Instagram

213 West Institute Place, River North

Explore this River North bar with its great selection of old-school arcade games, including many kinds of pinball and Pac-Man. Order either craft beers or signature cocktails to go along with your gaming. At a place like this, you’re guaranteed to have a fun time.


Cindy’s Rooftop

Bar Bucket List

Photo Credit: Cindy’s Instagram

12 South Michigan Avenue, The Loop

If you’re looking for one of the best views in the city, it’s Cindy’s Rooftop. Enjoy their signature cocktails and comfort food as well as the sweeping views of Lake Michigan.


The Signature Lounge

875 North Michigan Avenue, The Loop

Would you rather a city view or a water view? At The Signature Lounge, you don’t have to choose. Relax with a signature cocktail on the 96th floor of the John Hancock (we refuse to call it by it’s new name ,btw) building, and enjoy sweeping views across the city.


Kingston Mines

2548 North Halsted, Lincoln Park

Come to this blues joint on a night out with friends. Have some drinks and listen to some good tunes. Kingston Mines was founded in 1968, and is still going strong today.



Chicago Bar Bucket List

Photo Credit: Sidetrack Instagram


3349 North Halsted, Boystown

This hip Chicago gay bar features multiple levels and eight store fronts. Come here for a lively night of fun and drinks. They serve delicious fruit-slushee style cocktails that you won’t be able to get enough of.


The Violet Hour

1520 North Damen, Wicker Park

This bar is as unsuspecting as any other speakeasy. Enter via a door one block south of Damen and Milwaukee adorned by a single light bulb. They serve artisanal cocktails that are inspired by the pre-Prohibition era in an elegant, candle-lit setting.


The Whistler

2421 N Milwaukee, Logan Square

This perennially hip Wicker Park venue has got everything: great drinks, amazing music and a calendar full of ridiculous events to keep you coming back time and time again.


Pink Squirrel

2414 N Milwaukee, Logan Square 

Pink Squirrel may be a newer addition to the Chicago bar scene but it’s a necessary stop none the less. this old-school bar and bowling alley is serving up the old school drinks to match and you’ve just gotta check it out.


Best Intentions

3281 W Armitage, Logan Square 

Best Intentions is the late night bar of your dreams. I could tell you more about it, but it would totally ruin the atmosphere. You’re just gonna have to see for yourself.


Murphy’s Bleachers

Bar Bucket List Chicago

Photo Credit: Murphy’s Instagram

3655 N Sheffield, Wrigleyville 

Murphy’s is the quintessential Wrigleyville bar. Having opened as early as 1930 under the name Ernie’s Bleachers, a trip to Murphy’s is a trip down Chicago’s very own memory lane.



Chicago Bar Bucket List

Photo Credit: Delilah’s Instagram

2771 N Lincoln, Lincoln Park

Somewhere between a dive and a whiskey bar, Lincoln Park’s Delilah’s is a must-go for anyone looking for a chill night with great booze.


Maria’s Packaged Goods & Community Bar

Chicago Bar Bucket List

Photo Credit: Maria’s Facebook

960 W 31st, Bridgeport

This south side bar and community center is a liquor store, lunch counter, outdoor patio and events space all packed into one. And you totally need to see it.




Feature Image Credit: The Signature Lounge Instagram 


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Jennifer graduated from the Medill School of Journalism at Northwestern University in 2015. Her passions include reading, writing, and fitness. In her free time, she particularly enjoys exploring the city and brunching with friends. Her writing has appeared in magazines such as American Salon and Paste.

  • Please check out Old Grounds Social in Lincoln Park!!! It’s sooo cool!

    Apr 10, 2018
  • Check out OLD GROUNDS SOCIAL in Lincoln Park!!!

    Apr 10, 2018

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