1. Lighten up!
The city's official Christmas tree lighting ceremony comes only once a year! 2015's annual event comes with a twist: Both the ceremony and the tree itself move to Millennium Park after more than 40 years in Daley Plaza. Chicago's tree is a 63-foot Colorado spruce and promises to positively sparkle in its new home along Michigan Avenue—be there if you want to kick off the holiday season with Mayor Rahm Emmanuel. (Millennium Park, 55 N Michigan Ave, 5:30pm. Free)
2. Get Grime-y
Grimes (her real name is Claire Elise Boucher) takes the stage for the first of two nights at one of Chicago's most popular rock venues. Earlier this month she released her latest record, Art Angels, a collection of frantic pop songs that has received rave reviews from critics and listeners alike. (Metro Chicago, 3730 N Clark St, 6pm. $30, advance $26)
The Relax Attack Jazz Series pops up every Monday and Tuesday at the Whistler to give Logan Square locals a reprieve from the hectic stop-and-go of the work week. Pairing smooth tunes with some truly great cocktails, this is one jazz night you don't want to miss. Tonight, the Quin Kirchner Group takes the stage. And hey, you can even meet your bartender before you arrive. (The Whistler, 2421 N Milwaukee Ave, 9:30pm. Free)