PLEASE NOTE: Events may be postponed or simply canceled. Please call ahead to make sure they are still scheduled to take place. Vaccine requirements may also apply.

1. See The Legend 

Buddy Guy, the legendary blues singer and guitarist, finishes up his month-long residency at his namesake Chicago club, Buddy Guy’s Legends. Currently, his Friday show with John Primer is sold out, but head on over to the club to see his Saturday show with the Nublu Band or Sunday performance with Randy Johnson. January 28 – 30.

2. Celebrate Second City 

The iconic Second City has reopened. Get ready to laugh during Together at Last, a show that, according to Second City, dares to ask the question, “is anyone out there going to save us?” The show will make us laugh through our collective tears and frustrations about the pandemic, poking fun at our new and often uncanny realities.  January 28 – 30.

3. Sit with Silence

A silent film might just be the perfect recipe for cold, snowfallen weekends like the one ahead. If you agree, check out this weekend’s iteration of Silent Cinema at the Music Box Theatre. Presented by the Chicago Film Society, the Music Box will be playing The Freshman, starring Harold Lloyd. The theater calls this 1925 comedy an “unlikely smash,” a film about a college student’s quest to gain cache on campus, but whose only knowledge of college life has been absorbed from the movies. January 29.

4. A Little Cheesy

It’s a bar crawl done a little differently. The Mac & Cheese Crawl – Chicago’s Cheesiest Bar Crawl is hosted by Chicago Twenty Something and takes attendees to a slew of local venues in Wrigleyville. Munch on mac & cheese pizza from the HVAC Pub, carnitas and jalapeño mac & cheese from Moe’s Cantina, and more. January 29.

5. An Afternoon at the Orchestra

If you’ve been waiting for a nudge to visit the Chicago Symphony Orchestra, this is it. Dubbed a “Don’t-Miss” concert by the CSO, pianist Jan Lisiecki will perform a Chopin program of Opus 10 Etudes and a thrilling collection of nocturnes. Follow their heed and, indeed, “don’t miss.” Jan. 30.