5 to Try: Classic Cocktails
By Maura York, Chicago City Editor
Forget the low-carb beer and go retro instead. From a classic martini to a timeless Manhattan, find the best 1950s-era cocktails in Chicago.
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Jilly's
1007 N Rush St, Chicago, IL
With its extensive list of single malt Scotches, specialty whiskeys and cognacs, this Rush Street bar is about as classic as you can get. -
Coq d'Or
140 E Walton Pl, Chicago, IL
Four-ounce executive martinis (gin or vodka) have never gone out of style at the Drake Hotel's Prohibition-era bar. -
Matchbox
770 N Milwaukee Ave, Chicago, IL
Retro libations made with fresh ingredients, like gimlets with hand-squeezed lime juice, are specialities of this intimate West Town bar. -
Signature Lounge
875 N Michigan Ave, Chicago, IL
The Hancock Building's 96th floor bar boasts one of Chicago's best views, and superlative sidecars. -
The Bar at The Peninsula
108 E Superior, Chicago, IL
An inspired update of the classic martini bar within an upscale hotel.
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Tini Martini
2169 N Milwaukee Ave, Chicago, IL
Snug Bucktown/Logan Square bar that features rum drinks--and a full dance floor on weekends. -
Martini Ranch
311 W Chicago Ave, Chicago, IL
River North lounge with a stable of lush libations, such as peanut butter cup and dreamsicle versions of its namesake drink.

