1. See Dave Chappelle perform a surprise show
Duh. If this isn't the best thing to do in Chicago for the next week, we'd be surprised. Not only does the now-ellusive comedian rarely give shows, but Dave Chappelle is one of the most popular examples of American comedy across the globe—even though the sketch comedy show that made him famous ran for only three season nearly a decade ago. (Thalia Hall, 1807 S Allport St, 7pm. $67)
2. Put on your Christmas fancy pants
For what appears to be just a group of dudes in suits on the outside, this group has a lot of soul behind starched white button-downs and ties. This Grammy-winning choral group that tours the world makes a stop in Chicago for a brief two-night stay, the first of which is tonight. Enjoy their songs in the splendid surroundings of the Fourth Presbyterian Church, just off of Michigan Ave. (Fourth Presbyterian Church, 126 E Chestnut St, 7:30pm. $39-$61)
OK, this is the last time we'll talk about the holidays. Just kidding. The CTA's holiday train is one of those things we're still talking about even in July. You've barely got a month-long window to catch this incredible ride, so you might as well do it before everyone joins the bandwagon. Catch Santa leading the train car procession from 4-8pm on the Green and Orange lines. For more precise information and times, check the CTA's website. (Various station stops, 4-8pm. Free)