Chicago is one of the best bar towns on the planet, so it follows that the best Chicago bars are some of the best in the world. In order to make the list, each pub was considered according to the following criteria:
- Intriguing character, décor and history –have stood the test of time, occasionally attract celebrity patrons, and are sometimes featured in movies and TV shows;
- Food & drink – booze selection, quality/uniqueness of food;
- Music & Entertainment – live bands and/or killer jukeboxes, other performances and literary events.
- Sheffield's Wine & Beer Garden
3258 N. Sheffield Avenue (3300N, 1000W)
Chicago, IL 60657
On that first warm day of the year in Chicago that occurs sometime between March and July, nothing beats the beer garden at Sheffield's. The bar also features an impressive selection of beer (and wine), "barbeque in the back room," literary events, expressionist artwork, and classic Chicago architecture augmented by recent renovations and additions. When I am asked, "If you could only go to one bar for the rest of your life, what would it be?" For me, the answer is Sheffield's.
- Green Mill Cocktail Lounge
4802 N. Broadway (4800N, 1200W)
Chicago, IL 60640
Now over 100 years old, the Green Mill Cocktail Lounge is the crown jewel of Chicago's Uptown neighborhood and is the best jazz club in the known universe. Green Mill is a place for people of all walks of life to relax, enjoy martinis or Schlitz, and listen to some of the best music around, from traditional jazz to swing orchestras. The Green Mill even hosts the longest running poetry slam, every Sunday night.
Inspired by the Moulin Rouge in Paris (Red Mill), the Green Mill has attracted many celebrities through the years from Charlie Chaplin to Al Capone to Frank Sinatra to Bill Gates and has been filmed in The Untouchables, High Fidelity, and the 80s TV series, Crime Story. After much resistance, Uptown has finally succumbed to the regentrification surrounding it for the past 15 years now that Starbucks moved in. One has to wonder if this would have been possible if owner Dave Jemilo hadn't rescued the Green Mill from squalor in 1986 and restored its former luster, both in terms of décor and in hosting the best jazz around – a tradition that dates back to the club's beginning, so many moons ago.
- Hopleaf Bar
5148 N. Clark Street (5200N, 1500W)
Chicago, IL 60640
Well, the secret is out: one of the best neighborhood bars in Chicago is not in Lincoln Park, Bucktown or even Lakeview. It's in the far north Chicago hamlet of Andersonville, and its name is the Hopleaf Bar. Locals know it simply as "Hopleaf" and desperately try to guard its eroding anonymity from those bar-hopping further south.
Even though the weekend crowds can get brutal, Hopleaf remains true to its design as a very cool neighborhood joint that draws its loyal and increasing following from its laid-back vibe, tasteful decor, eclectic music, the best steamed mussels in the city, a most pleasant outdoor beer garden, and one of the best "hop" selections in the city with Belgian beers (even trappist ales) on tap as their specialty. Since 1992.
- Goose Island Brew Pub
1800 N. Clybourn Avenue (1800N, 1000W)
Chicago, IL 60614
This original Goose Island location on Clybourn is one of the most universally loved pubs in all of Chicagoland. Those who are hungry will appreciate the endless rotation of hand-crafted brews made with superb quality. Those who hunger will appreciate the well-designed menu that provides the ideal accompaniment to the fine selection of ale.
Those who are bored will appreciate the pool tables, the Golden Tee and the general camaraderie that accompanies a room full of people getting sauced on some of the best beer they've ever had. As a result, few pubs in the city are more talked about, recommended, or more frequented by locals and travelers than the Goose Island Brew Pub since it opened in 1988. While their newer location in Wrigleyville is hard to beat after a Cubs game, the original location remains a true Chicago classic.
- Duke of Perth
2913 N. Clark Street (2900N, 600W)
Chicago, IL 60657
While being cheaper than a trip to Edinburgh and more pleasant than a poke in the eye, the Duke of Perth is the best Scottish pub in Chicago. Okay, it's only one of two Scottish pubs in Chicago, but it's still pretty cool (and we like Ole St. Andrew's Inn further north as well).
And folks, it's a pub. There are no televisions at the Duke, so you may have to talk to somebody. Known for its $8 all-you-can-eat fish and chips on Wednesdays and Fridays, 90 blends of single-malt scotch (best variety in Chicago), and very cute waitresses (hand-picked by the owner), the Duke has something for everyone and their brother – which causes the pub to get very crowded, so get there early. Since 1989.
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