Matthew Santos at Webster Wine Bar, 1480 W. Webster Ave., 9 p.m.
Santos has established himself as one of the best voices to emerge from Chicago with collaborations with Lupe Fiasco earning him two Grammy nominations. He'll bring his unique mix of indie-rock, alternative, rock, folk and soul music to Webster's Music Monday for a three-hour performance with no cover.
The Female Funnies at Zanies, 1548 N. Wells St., 8:30 p.m.
A ladies night of laughs hosted by "Chicago's Latin Diva of Comedy," Patti Vasquez featuring 5-10 of Chicago's funniest female comics. Tickets for the show are $10 with the minimum purchase of two food items or drinks.