College kids hang with jazz lifers at this 68-year–old joint, the only spot in town that books an all-star lineup and takes reservations. Cover isn’t cheap—tickets run up to $40 on weekends—but that extra dough gets you access to such vets as Pat Martino (playing a six-show residency this month) sans those pesky lines outside Green Mill.
South Loop, 806 S. Plymouth Ct., jazzshowcase.com
The Empty Bottle
Despite the area’s shift toward the boutiquey, this rock dive remains as stained and stanky as in its mid-’90s heyday. No matter: If the Bottle is skimping on beautification, it’s because its talent-buying savants book the best touring bands indie money can buy. Ukrainian Village, 1035 N. Western Ave., emptybottle.com
Stellar programming and a benevolent staff keep this secluded frumpster hopping, but it’s the laid-back patrons that make it great. Crowds sport plaid, but any fan will feel a sense of belonging in the modest music room. West Town, 1354 W. Wabansia Ave., hideoutchicago.com
This cocktail lounge is fast becoming the one-stop spot to see local talent before they break out—a farm league for Chicago’s greater music scene. It’s still a bar first and a venue second (you won’t see any marquee acts), but expect arty if embryonic programming from avant-jazz to funk and soul DJs. Logan Square, 2421 N. Milwaukee Ave., whistlerchicago.com