Chicago’s Most Iconic Bars

By Melanie Falina

One of the most unfortunate realities about smaller towns is their lack of options – fewer places to eat and drink, fewer places to learn and explore, to enjoy the arts and culture, the list goes on. But this isn’t a problem in the Chicagoland area and most Chicagoans relish in the constant abundance of choices for every occasion and walk of life. But with a plethora of choices in a city as large and dynamic as Chicago, sometimes it can feel as if there are too many options available. So if you’re looking to find some of the essential places to meet up with friends and have a cocktail in the Windy City, here are some of Chicago’s most iconic bars to add to your schedule this weekend.

Hala Kahiki Tiki Bar & Lounge
2834 River Road
River Grove, IL. 60171
(708) 456-3222
www.chicagotikibar.com

Even amid the humid and blazing temps in Chicago every July and August, the Chicago-area is far from a tropical paradise. But the Hala Kahiki Tiki Bar & Lounge has been doing “tiki” long before it became trendy, and as close to Chicago as in near-by River Grove, Illinois. With a history dating back to the early 1950s in the Bucktown neighborhood of Chicago, the Hala Kahiki began serving up not just an array of tropical drinks, but an entire tropical experience. Enjoy specialty food and drinks inside the bar decorated with the most charming Tiki decorations, light fixtures, and  Witco Tiki furnishings, or relax in fresh air in the Tiki patio garden, either way, you’re likely to leave with a smile on your face and a tiny umbrella tucked behind your ear.

Billy Goat Tavern
430 N. Michigan Ave.
Lower Level
Chicago, IL. 60611
(312) 222-1525
www.billygoattavern.com

Even the younger generation of Chicago Cubs baseball fans know at least a little bit of the story of the “Billy Goat Curse.” Back in 1945, then-owner of the Billy Goat Tavern, William Sianis, brought his pet and the mascot of the tavern – a goat – to Game 4 of the World Series at Wrigley Field. But Sianis and his goat were ejected from the game, and the legend states that Sianis placed a curse on the Cubs preventing them from ever winning a World Series Championship. The fact that it took the Cubs until 2016 to finally bring it all home only fueled the rumored curse. But supposed curses aside, there are other great reasons to pay a visit to the original Billy Goat Tavern in downtown Chicago. From the “Cheezborger! Cheezborger…No Pepsi – Coke!” antics that inspired the classic Saturday Night Live skit to being a hangout for the famous Chicago columnist Mike Royko for decades, the Billy Goat Tavern has been overflowing with personality since 1934.

The Green Mill
4802 N. Broadway St.
Chicago, IL 60640
(773) 878-5552
www.greenmilljazz.com

Even with a rich history and architectural treasure-troves still standing in Chicago, there are few still-operating establishments that can say that cronies of the famous, and infamous, mafia-boss Al Capone were regulars – but The Green Mill sure can. Designed with Paris’ Moulin Rouge in mind, The Green Mill opened its doors in the Windy City in 1909. Located in Chicago’s Uptown neighborhood, not only did the Green Mill host the best of jazz during the jazz era when it was thriving, an actual speakeasy during the Prohibition, and continues to offer the best jazz and entertainment to this day. From live music nightly to regular poetry slams and an array of classic cocktails and all-round class, an evening spent at The Green Mill should absolutely be required for validating accepted Chicagoan-residency.

Related:  Best Oldies Music Bars In Chicago

Kingston Mines
2548 N. Halsted St.
Chicago, IL. 60614
(773) 477-4646
www.kingstonmines.com

Although the genre of blues music is believed to have originated in the Mississippi Delta, it was the Great Migration that brought many artists to the Chicago area, and hence Chicago became known as the home of the blues, and it’s a title that Chicago accepted graciously. Today, one of the places to revisit a legendary music scene that blossomed here in Chicago is at Kingston Mines. Located int he Lincoln Park area of the city, Kingston Mines is both the largest and the oldest continuously operating blues club in the city. Established in 1968, Kingston Mines has hosted the biggest and best blues legends over the years, and still overs live music seven days a week. With a motto of “Hear blues – drink booze – talk loud – you’re among friends!” – what more could anyone want?

The Signature Room at the 95th
875 N. Michigan Ave.
Chicago, IL. 60611
(312) 787-9596
www.signatureroom.com

95 floors above a thriving metropolis like Chicago is sure to offer some of the most amazing views of the city, and The Signature Room at the 95th all way up atop the John Hancock Center building does not disappoint. The floor-to-ceiling windows with panoramic city views are high up enough to see much of city, but not too high to feel lost in the clouds and poor visibility. The Signature Room hosts both a stately lounge, as well as a restaurant offering upscale dining. With some of the city’s best contemporary cuisine and signature cocktails at the ready, The Signature Room at the 95th will remind even the longest of city residents just how stunning of a city Chicago truly is.

Related: Best Places To See Cover Bands In Chicago

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