1. Ghost Town
Start this spooky season off with a scream at opening weekend of Nightmare on Clark Street, a pop-up haunted house and Halloween-themed dining experience that gives Wrigleyville nightlife a new face. Round off your evening at the haunted patio bar if you dare. October 1–31. nightmareonclarkst.com
2. Gallery Walk
See the streets of Andersonville transform into an immersive, walk-through art gallery at Andersonville Arts Weekend, a three-day festival celebrating art in many forms — visual, performance, culinary, and more. Cater the weekend to your liking with a self-guided art walk or multi-stop wine tasting. September 30–October 2. andersonville.org
3. Going Deutsch
We can’t think of a better way to kick off the month than Oktoberfest, and Naperville is coming through with a great one. Boasting German cuisine, lots of beer, plenty of polka, and a slew of yard games, the heated tent at Naper Settlement has you covered. September 30–October 1. napersettlement.org
4. Laugh Track
Comedian Cristela Alonzo, the eponymous star of ABC’s Cristela and the wit behind two Netflix comedy specials, is bringing her tour to Chicago. Enjoy a night of drinks and laughs at The Den Theatre’s main stage venue. September 30. thedentheatre.com
5. World Stage
In its 22nd year, Chicago’s citywide World Music Festival will celebrate and represent 22 countries and global regions with live music performances from more than 30 . September 30–October 9. chicago.gov