5:00 Neil Dixon Smith at Northman Riverwalk
5:30 Chicago Jazz Orchestra with Thaddeus Tukes at Jazz Showcase, $25-40
6:00, 8:15 The Clif Wallace Big Band at Andy's, $15
6:00 Pro/Am Open Mic Night at On Tour Brewery
6:00 Eddie Palmieri Salsa Orchestra at Jay Pritzker Pavilion
6:00 Open Mic/Open Jam Monday with host Aaron Kelly at Preservation Geneva
7:00 Whiskey Bob Taylor hosts Open Mic Night at Montrose Saloon
7:00 Blake Burkhart, Zack Fedor & The Long Goodbyes, ++ at Reggie’s Music Joint, $10, South Loop Comedy & Music
7:00 Wednesday, Squirrel Flower, Tenci at Metro, $20-25
7:00 Northern Lighthouse, Sunbunny, Juan Flores at Cafe Mustache
7:00 Wabi Sabi with caller Georges Augustin at Irish American Heritage Center 4th Floor Ballroom, $5-10, Contra & Square Dance, Lesson at 6:30
7:00 Bluegrass Jam at The Atlantic Bar & Grill
7:00 Space Staff Showcase at SPACE Evanston
7:00 Jay O'Malley acoustic at 115 Bourbon Street Merrionette Park
7:00 Outcast Jazz Band at Roxy Lockport, $10
7:00 The Corner at Promontory, $15-25
7:30 Matt Heckler, Johno Leeroy at Schubas, $15-20
7:30 Tommy Muellner’s Jazz Jam Mondays at Borelli’s Pizza
x 8:00 Joel Paterson & Friends with Oscar Wilson at Green Mill, $10
8:00 Extraordinary Popular Delusions at Beat Kitchen
8:00 Monday Night Open Jam hosted by Cosmic Jaywalkers at Golden Dagger
8:00 Surabhi Ensemble at City Winery, $20-30
8:00 Quenehen/Cellier Duo, Bradfield/Simpson/Philion/Swan at Elastic Arts, $15, Anagram Series
8:00 Stardust Big Band at Gallery Cabaret
8:00 Ivan Singh & Dan Souvigny with Aidan Epstein and Jeremiah Collier at The Humboldt Jungle, $10
8:00 Open Mic hosted by Sean Shiel at Mackey’s Hideout McHenry
8:30 Bath Rooms/Disco Nap at California Clipper
9:00 Fake English, The Deals, The Bascinets at Empty Bottle
9:00 Punk Rock Monday DJ Bloodshot Scot at Delilah’s
9:30 DJ Adam Black at Emporium Wicker Park, Manic Mondays Industry Night
10:00 Mistahan, Nik Ill, DB Stereo, Juice Man at Prysm, $10-15, Industry Mondays
?:00 Chez Butter at Beverly Arts Center, Music Mondays
x 8:00 Joel Paterson & Friends with Oscar Wilson at Green Mill, $10