• Take a ride north to the 110-year-old Green Mill for an evening of live music
• Catch a local jazz legend like Patricia Barber and her amazing band
• Dine preshow at one of Chicago’s standout new restaurants

If you thought Wrigley Field was the oldest and most hallowed landmark on the north side of Chicago, think again: The Green Mill Cocktail Lounge turns 110 in 2017, and some would argue it’s seen more consistently great performances than a certain storied ballpark to the south. From its early years as a roadhouse to its heyday as a haunt of Al Capone’s, this unassuming tavern—located in the Uptown neighborhood, a 30-minute drive north of the Conrad—has managed to stay vital and relevant on the jazz circuit, with local and national acts performing regularly. (It’s also home to the raucous Uptown Poetry Slam, a crowd favorite since 1986.) Pretty much any night is a good night at the Green Mill, but if you’re able, try to catch a set from Patricia Barber and her trio or quartet. A gifted vocalist, pianist, and bandleader, Barber is a second-generation Chicago musician (her dad was in Glenn Miller’s orchestra), and she’s been a fixture at the club for decades. Dinner before the show? Start your night a few blocks west in Ravenswood, where you’ll find one of Chicago’s best new restaurants, called simply Elizabeth. It’s run by the brilliant self-taught chef Iliana Regan, whose fluency with foraged ingredients translates into pure deliciousness on the plate.

The Green Mill Cocktail Lounge is located in Uptown, a 30-minute drive (without traffic) north of the Conrad Chicago; Elizabeth is 1.6 miles due west, via West Lawrence Avenue, in Ravenswood.

THE GREEN MILL COCKTAIL LOUNGE: 4802 N. Broadway St.; 773-878-5552; greenmilljazz.com

ELIZABETH RESTAURANT: 4835 N. Western Ave.; 773-681-0651; elizabeth-restaurant.com