Monday

Blues at the Quarry

When dusk hits, this community space becomes one of the most reliable music venues in town. If you’re lucky, you’ll brush up against history: Recurring performers include Willie Dixon’s backing band and Elmore James Jr., son of the slide guitarist. $10. 2423 E. 75th St., South Shore, thequarrychi.com
 

Tuesday

Trivia Tuesdays at the Globe Pub

You don’t have to be a Jeopardy! champion to enjoy this nerdy night. But if you want to win? That’s a different story. Quizmaster Dave Ahrens’s questions are laughably arcane and specific (think Star Trek dialogue). $5 donation. 1934 W. Irving Park Rd., North Center, theglobepub.com
 

Wednesday

Comedy Open Mic at Cole’s

It’s been featured on the Netflix series Easy and has hosted surprise appearances by the likes of Hannibal Buress, so this not-quite-amateur night isn’t really a secret anymore. Still, it remains the essential destination to catch up-and-coming comics. Free. 2338 N. Milwaukee Ave., Logan Square, colesbarchicago.com
 

Thursday

MaryOke Karaoke at Hamburger Mary’s

Once a week the restaurant’s second-floor lounge transforms into the premier local spot for karaoke. On occasion, it’s possible to hear actual opera singers belt Disney soundtracks and see theater professionals strut through show tunes. Free. 5400 N. Clark St., Andersonville, hamburgermarys.com
 

Friday

S. Joel Norman at Tack Room

With Thalia Hall, Dusek’s, and Punch House also under the same roof, this piano bar can seem like an afterthought. But when Norman is tickling the ivories, it’s the main draw. Sing along as the versatile maestro tries anything you request, even beatboxing. Free. 1807 S. Allport St., Pilsen, tackroomchicago.com
 

Saturday

Midnight Movies at Music Box Theatre

At 11:59 p.m., the finest screening room in town loads up the projectors with a smartly curated rotation of cult classics, from the newish (Mad Max: Fury Road) to the oldish (Boyz N the Hood) to the ageless (The Rocky Horror Picture Show, of course). $9–$12. 3733 N. Southport Ave., Lake View, musicboxtheatre.com
 

Sunday

Queen! at Smartbar

The neon basement of the Metro has always been a guaranteed blast on Sundays, but things cranked up a few notches when this LGBTQ-focused DJ residency debuted seven years ago. Admission varies. 3730 N. Clark St., Wrigleyville, smartbarchicago.com