Chicago is offering a variety of alternative events for those looking to avoid traditional Valentine’s Day celebrations. For residents who are single or prefer a non-romantic approach to the holiday, several gatherings across the city aim to provide different experiences.
The Drunk Shakespeare Society will present “Drunk Romeo and Juliet” at The Lion Theatre in Downtown Chicago from February 4-15. According to organizers, the performance features one professional actor who consumes five shots of whiskey before acting out the story in a library setting filled with 10,000 real books. Tickets start at $49.
For young people aged 25 and under, the National Museum of Mexican Art’s youth initiative is hosting its annual Anti-Valentine’s Day event on February 6 at the Little Village Fire Station. The gathering includes crafts, pizza, and free sexual health resources. Organizers say it offers a safe environment without social stigma or financial barriers for accessing information about health.
About Last Night, originally started in San Francisco as a storytelling series focused on awkward dates, brings its Anti-Valentine’s show to Chicago for the first time on February 10 at The Den Theater in Wicker Park. Local storytellers will share tales of heartbreak and disappointment during this comedic event. Tickets range from $20-$30.
Sleeping Village in Avondale will host Heartthrob Hangout on February 13—a music and game show intended as counter-programming to typical Valentine’s events. The evening features performances by local bands including Olivia and the Lovers, Naked Brunch, and Em Grace & the Undercuts. Tickets cost $15.
Timber Lanes Bowling Alley in North Center will offer a singles mixer on Valentine’s Day itself (February 14), where attendees can meet others while bowling. Admission is $25 and includes unlimited bowling, shoe rentals, and a drink ticket.
On the same night at Lincoln Hall in Lincoln Park, Mortified Chicago presents its Doomed Valentine storytelling show featuring individuals recounting embarrassing adolescent stories about crushes and unrequited love. Tickets begin at $33.
The Salt Shed in West Town teams up with The Music Box for Crying At The Shed Film Fest from February 12-14. The festival focuses on films about complex modern relationships—including titles like “Licorice Pizza,” “Her,” “La Chimera,” “Lost In Translation,” and “Beginners.” There will also be live music by Lael Neale on opening night and themed activities inspired by some of the films shown.
Bottom Lounge hosts Sgt. Goof’s Lonely Hearts Club Ball on February 15 with performances from local pop artist Goof alongside other musicians such as Oux, Multimagic, and Molly Coleman. Tickets start at $32.
Simone’s Bar in Pilsen will feature an anti-Valentine’s drag brunch hosted by House of Haüs Productions from 1-3 p.m., also on February 15. Drag performers Jasmine Phoenix, Vanya Dee, and Hunter Diamond headline this event; general admission is available online for $18 or potentially $15 at the door if not sold out.
Ritual Rhythms Chicago returns with Love Is LoveFest at Newport Theater on February 21. This music show celebrates diverse expressions of love through performances by gothic country artist Iris Marlowe along with dance acts Zahradka Tonic, Tender Blossom, Juniper Faewild, Vilma Noir, Schmoo and SerpentFuze twins. Tickets start at $28.50.
