A packed house watches the Gilad Hekselman Trio at the Green Mill. (Keri Wiginton )
4802 N. Broadway 773-878-5552
Looks like: The encyclopedic definition of an old-school jazz bar, minus the cloud of cigarette smoke and with the addition of a topless Roman statue
Smells like: Nothing noticeable
Sounds like: Live music, but everything else depends on who's on stage. You might hear a jazz quartet play to a hushed crowd, or an orchestra's brassy swing music might pack the dance floor.
If history were gray dust, Green Mill would be covered in a thick layer of the stuff. For more than a century, this Uptown bar's blinking green-and-white sign has been a bat signal for jazz lovers, mobsters, musicians and Prohibition-era bootleggers. It's a storied past that plenty of newly opened speakeasy-style bars have tried to replicate, but once you step foot inside Green Mill, it's clear that there's no substitute for authenticity.
Even as a band's just tuning up around 9 p.m., the walls seem to reverberate with the building's cumulative sonic history. Yes, you'll have to pay a $4-$15 cover, but I promise that the ambiance the band provides is worth the cost. (Take the Red Line to the nearby Lawrence "L" stop and you'll save money that you would have spent on a cab.) You don't have to know an alto sax from your elbow to enjoy the music, but being a hopeless romantic will greatly enhance your experience here. Need inspiration? Read "The Great Gatsby" or cue up "Chicago."
On weeknights when smaller acts play, arriving 20 or 30 minutes before show time should guarantee you a prime seat at the far curve of the bar—a solid, dark wood wonder that's as deep as my entire arm. There, you'll have an unobstructed view of Green Mill highlights: the stage (obviously), but also the coffee table behind the bar that's been crafted into a sort of shrine to Al Capone, who used to pack his henchmen into one of the curved booths that line the north wall. You'll also notice Ceres, a Roman goddess statue that was rescued from the bar's metaphorical cobwebs, as well as wood-framed landscape paintings lit by strange, pinkish bulbs.
Drink it all in. Dress up a bit—you won't be out of place. Order a rye Manhattan or sip a split of sparkling wine from a coupe glass. Sit up straight. Don't talk during quieter performances or prepare to be shushed by the staff. Put your phone away. Tap your toes. On a weekend night when the bar is packed to capacity, find an extra inch at the bar anyway. Step into the Green Mill time machine and enjoy the soundtrack.