Music and movies collide at the 8th annual CIMMfest. Join filmmakers, musicians and dedicated fans for a four-day celebration with more film screenings, performances, panels and concerts than you can handle. (Various locations throughout Chicago, Wed–Sun. $79–$149)
Hunt for the perfect vintage couch or piece of art at Vintage Garage, a monthly market set up in an Uptown parking garage. More than 100 vendors sell everything from clothes to vinyl every third Sunday of the month. (Vintage Garage, 5051 N Broadway, Sun 10am–5pm. $5)
Joshua Tillman, former Fleet Foxes drummer, brings his music to Chicago as Father John Misty. The quick-witted singer, songwriter, guitarist and drummer is sure to entertain with his wry humor. (Riviera Theatre, 4746 N Racine Ave, Fri 8pm. $34)
Get ready for Pinot Days, where guests can talk with winemakers and taste pinot wines and food pairings from local bars and restaurants. More than 65 wineries will be in to Chicago for the event, so guests can try offerings from all over the country. (Navy Pier, 600 E Grand Ave, 2pm. $75)
5. Fraturday
The sun is shining upon those who peaked in college. This weekend is Fraturday, an epic flip cup tournament hosted by Chicago Sport & Social Club. Make sure your Vineyard Vines and Chubbies Shorts are up to par and you could win a best-dressed prize. (Joe's Bar, 940 W Weed St, Sat 11am. $30 to watch, $160 for teams)