Show all the holiday cheer you can muster at Do-It-Yourself Messiah, a community sing-a-long of George Frideric Handel's classic holiday tune backed by an orchestra of Chicago-area professionals and hobbyists. It's a tradition that's goes back to 1976, bringing together thousands of Christmas revelers. (Harris Theater, 205 E Randolph St, 7pm. $15)
2. Lighten up
You'll have to travel outside of the city to attend this one-of-a-kind celebration, but the Magical Animated Holiday Light Show is worth the trek. Projected on the facade of the Hampton Hotel, this 3D Christmas light show is set to seasonal music that is sure to raise your spirits. (Randhurst Village, 1 Randhurst Village Dr, 6pm. Free)
Gaze at the stars during the shortest day (and longest night) of the year—the winter solstice. Adler Planetarium lets visitors into the museum's Doane Observatory, one of the most powerful telescopes available in the area for public use. (Adler Planetarium, 1300 S Lake Shore Dr, 1–7pm. Free)