1. Flyover Country

An annual favorite drawing in crowds over a million, the Chicago Air and Water Show is a free aerial performance show featuring demonstrations from legendary military and civilian flight crews. For the best views of these low-flying jets (complete with stunts!), we recommend setting up camp at North Avenue Beach. Aug. 20–21. chicago.gov

2. Thanks, It’s Vintage

The Thalia Hall Vintage Market is partnering with Illinois Vintage Fest to bring Chicagoans a can’t-miss smorgasbord of vintage art and collectibles, featuring live music from a local DJ. Aug. 21. do312.com

3. BYOB (Bring Your Own Bib)

Ribfest is back and (lovingly) messier than ever, bringing a three-day festival filled with food, beer and live entertainment to Lincoln, Damen, and Irving Park. Aug. 19–21. Chicagoevents.com

4. Street SmArt

Glenwood Avenue Arts Fest may just be everything you’re looking for in a weekend festival, boasting three days of live music, showcasing the works of more than 100 local artists, and offering a wide variety of local food and craft beer. Aug. 19–21. glenwoodave.org

5. Dream A Little Dream

Fans of Ella Fitzgerald, Amy Winehouse, and the likes, this one’s for you! Aire Rooftop Bar is hosting a tribute to female jazz icons through the end of August that will keep you humming all week like no one’s listening. Aug. 19–21 and through Sept. 2. feverup.com