A Look Ahead at Chicago Lit: May

by Kayleigh McNamara

Maiden, that read'st this simple rhyme,

   Enjoy thy youth, it will not stay;

Enjoy the fragrance of thy prime,

  For oh, it is not always May! 

Enjoy the Spring of Love and Youth,

   To some good angel leave the rest;

For Time will teach thee soon the truth,

  There are no birds in last year's nest!

– Henry Wadsworth Longfellow 

Let us all enjoy this beautiful spring in Chicago without wishing it away to summer. May has an exciting lineup of literary events to help you do just that. 

Beginning Tuesday, May 5, Chicago’s inaugural poet laureate, avery r. young, will be hosting “chi-soul workshops” through the Chicago Public Library. All writers are invited to the Austin branch (5615 W Race Avenue, Chicago, IL 60644) to create poetry centered around the Chicago experience. This program will run through November. 

Thursday, May 7, Women & Children First will be hosting Gina Frangello and Elizabeth Crane to celebrate the release of their latest work. At 7 p.m., head to the bookstore (5233 N Clark Street, Chicago, IL 60640) to hear the authors in conversation with Megan Stielstra. Admission is free but advanced registration is required.

Also on May 7,  Sparks & Wiry Cries has partnered with Fourth Coast Ensemble to produce the 2026 songSLAM event. The event will take place from 7–9 p.m. at the Koval Distillery Tasting Room (4241 N Ravenswood Avenue, Chicago, IL 60613). Join to see live original work performed for the chance to win cash prizes. Stacy Garrop will emcee. Learn more here. 

Friday, May 8 is opening night of the Festival of Independent Artists. Be sure to catch Art Speaks from 5–9:30 p.m. at the Stan Mansion (2408 N Kedzie Boulevard, Chicago, IL 60647) to hear seven different writers discuss their ekphrastic collaboration with seven visual artists. Tickets start at $25. 

The ballet inspired by Sandra Cisneros’s quintessential Chicago novel, The House on Mango Street, has already sold out its first show. Grab tickets for the May 9 performance while you still can! Ballet 5:8 will be performing at the Logan Center for the Arts (915 E 60th Street, Chicago, IL 60637) at 2 p.m. with an art exhibit to open one hour before the show. 

Wednesday, May 14, founding president of the Chicago Writers Association, Randy Richardson will be at The Book Cellar (4736 N Lincoln Avenue, Chicago, IL 60625) to celebrate the release of his novel, Another Havana Hangover. The event begins at 6:30 p.m. and is free to attend, however an RSVP is suggested. 

The Chicago Latino Theater Alliance (CLATA) presents the third year of inicios: Chicago Latine Playwright Festival at Collaboraction Theatre Company (1575 N Kimball Avenue, Chicago IL 60647). The festival is free to attend and takes place over the weekend of May 15. Six plays have been crafted by CLATA’s playwriting cohort with guidance from Dr. Rey Andújar. Learn more about the readings here.

Sunday, May 17, David Sedaris will be at the Auditorium Theatre (50 E Ida B. Wells Drive, Chicago, IL 60605). Be sure to attend the event so as not to miss Sedaris’s thought provoking wit, a behind the scenes look at his new unpublished stories, and a book signing. Tickets are about $80 and can be purchased here. 

The Chicago Literary Hall of Fame is excited to announce our collaboration on the May 17 Sunday Reading Series. Kenyatta Rogers from the CLHOF Board of Directors will host. Go to Hungry Brain (2319 W Belmont Avenue, Chicago, IL 60618) at 7 p.m. to hear readings from Noa Micaela Fields, Tsehaye Hébert, and Riva Lehrer. 

There are only three spots left on the CLHOF’s Downtown Chicago Literary Walking Tour! Reserve your tickets for $25 and meet us at the Palmer House (17 E Monroe Street, Chicago, IL 60603) at 2 p.m. on Wednesday, May 20. “Explore the city through a literary lens.” 

Friday, May 22, Zayd Ayers Dohrn will be at City Lit Books to discuss his memoir, Dangerous, Dirty, Violent, and Young about his childhood raised by parents on the run from the FBI. The event takes place from 6:30 to 7:30 p.m. and is free but an RSVP is requested. Copies of the book can be preordered here. 

Keerah, a play written by Netta Walker and directed by McKenzie Chinn, will debut Friday, May 29 at Definition Theatre (1160 E 55th Street, Chicago, IL 60615). The story is set in a Chicago neighborhood in the midst of gentrification and follows two young writers as they grapple with the world around them. Tickets start at $25. 

Saturday, May 30, the Chicago Indian Literature Festival will take place from 9 a.m. to 6 p.m. in the Gold Room of the Congress Plaza Hotel (520 S Michigan Avenue, Chicago, IL 60605). This festival celebrates the diaspora of Indian culture in the Midwest with author talks and panels, book launches, and more. Tickets begin at $15 and can be bought here. 

If you’re missing Volumes Bookcafe (as we all are), and you want to keep up with all the latest and greatest events, you can read more from Volumes’s former-owner, Rebecca George’s new literary calendar, Lit Circle.