6:00, 8:15 The Heritage Jazz Orchestra at Andy’s, $15
6:00 Pro/Am Open Mic Night at On Tour Brewery
6:00 Atomic Bingo at The Beacon Tap Des Plaines
6:00 Monday Night Pool League at Whiskey Girl Tavern, APA Pool League
6:30 Flavor Flicks at Uncommon Ground Lakeview
7:00 Blake Burkhart, Chris Trani, Kieron Harrell, Julia Stoyanova, Calvin Evans, Zack Fedor & The Long Goodbyes at Reggie’s Music Joint, $10, South Loop Comedy & Music
7:00 Twrp, Magic Sword at Metro, $25-30, $85 VIP
7:00 Love Train tribute to O’Jays, Ladi Soul, Bernard Crump & The Mecca All-Star Band, Big Fred’s Smoke Meats Food Truck at Promontory, $25, Mecca Monday, Soul Fest
7:00 MHC Trio, Eric Binder Trio at Cafe Mustache
7:00 Marques Carroll at Green Line Performing Arts Center, First Monday Jazz
7:00 The Resurrection Marys with caller Andrea Craft at Irish American Heritage Center 4th Floor Ballroom, $5-10, Contra & Square Dance
7:00 “An American Tail” screening at Paramount Theatre Aurora, $1
7:00 Trivia Night at Madcats Palatine
7:00 Trivia Night at Double Clutch Brewing Company Evanston
7:00 Trivia Night at Whiskey Girl Tavern, Stewpendous Productions
7:00 Whaddayaknow Trivia at Leaderbar
7:30 DuPage Community Concert Band at Belushi Performance Hall, McAninch Arts Center, College of DuPage Glen Ellyn, $7
7:30 Tom M. Muellner’s Jazz Jam Mondays at Borelli’s Pizza
x 8:00 Joel Paterson & Friends at Green Mill, $10
8:00 Paris Chansons at SPACE Evanston, $20-45
8:00 Annie Dirusso, Hannah Cole at Lincoln Hall, $20
8:00 Show Dem Camp, Moelogo at Schubas, $25-30, $80 VIP
8:00 Extraordinary Popular Delusions at Beat Kitchen
8:00 Crocodiles, Saint Pé, The Bingers at Beat Kitchen, $15
8:00 Storm Large at City Winery, $22-35
8:00 Jimmy Bennington’s Colour And Sound, Paul Hecht Quartet at Elastic Arts, $15, $10 w/ student id, Anagram Series
8:00 Ivan Singh & Friends, Comedy at The Humboldt Jungle, $15
8:00 Open Mic Night Mondays with host Whiskey Bob Taylor at Montrose Saloon
8:00 The Masters Collection at Golden Dagger, Monday Night Open Jam
8:00 Deanna Ortiz, Derry Queen, Andy Rowell, Claire McFadden, Michael Serio, hosted by Michael Serio at Sleeping Village, $5, $1 PBRs, An Evening of Laughter
8:00 Bingo with Tyler at Reggie’s Roof Deck
Mon 5/1? 8:00 Karaoke with Colleen at Jesse’s Tavern Chicago Ridge
8:30 Annie Fish, Evan Main at California Clipper
9:00 Allá, Chebaka, Kaczynski Composite Sketch at Empty Bottle, Free Monday, No Sé Discos Label Showcase
9:00 Acoustic Open Mic hosted by Buschy at Four Treys
9:00 Punk Rock ? at Delilah’s, Punk Rock Monday
9:30 Monday Night Karaoke at The Thirsty Tavern
10:00 Industry Mondays at Prysm, $10-15
Mon 5/1? 10:00 DJs Equip & Mukqs at Cole’s Bar, Video Game Music DJ Night
x 8:00 Joel Paterson & Friends at Green Mill, $10