May marks that time of the year when events, both public and private, take advantage of the favorable weather and migrate from the indoors to the outdoors. Even many benefits, galas and fundraisers move outdoors this month.
The Women's Board of the Lyric Opera of Chicago hosts the triennial Lyric Wine Auction on May 8 and 9. John Holmes and Jenni Sorenson are co-chairing the event, which features honored guests French winemakers Pierre Lurton of Château Cheval Blanc and Erwan Faiveley of Domain Joseph Faiveley. French culture will be celebrated at the Woman's Board of the Alliance Française de Chicago's biennial gala on May 9 at the Four Seasons Hotel Chicago. That evening event honors Carol and Jeffrey Horvitz, who have contributed their remarkable collection of French art to the Art Institute of Chicago. Steppenwolf Theatre Company celebrates five decades of innovative theatre at its Steppenwolf Gala 2026 at Rockwell on the River, also on May 9.
The Music Institute of Chicago's 95th anniversary gala is May 18 at the Four Seasons Hotel Chicago. It supports music education and honors the Lyric Opera of Chicago with the Dushkin Award, and Marta Aznavoorian with the Colburn Award for Teaching Excellence. The Cultural Visionary Award goes to Donna La Pietra and Bill Kurtis (who retires from NPR's weekly show "Wait Wait… Don't Tell Me!" this month).
DANK Haus German American Cultural Center holds its annual gala indoors at the center on May 16. Celebrate German culture outdoors at the 27th annual Maifest at Lincoln and Western, May 29–31. Think of Maifest as Oktoberfest in May.
At the invitation of my good friend and dedicated Anti-Cruelty volunteer, Sarah Ames, I attended an Anti-Cruelty awards brunch at the shelter in March. Their next big event is an outdoor fundraiser: the 32nd annual BARK: Walk for Chicago's Animals on May 30 at Lincoln Park Grove 2.
May is Asian American and Native Hawaiian/Pacific Islander (AANHPI) Heritage Month. The Gene Siskel Film Center hosts the 29th annual Asian American Showcase on May 7–12. This month the Forest Preserves of Cook County sponsor free outdoor cultural events celebrating AANHPI Heritage Month, including AANHPI Month Performances by Mandala South Asian Performing Arts on May 16 and 17 at three Cook County Forest Preserves.
May is also Jewish Heritage Month/Jewish American Heritage Month. Featuring a re-creation of the secret annex in the Anne Frank House in Amsterdam, "Anne Frank The Exhibition" at the Griffin Museum of Science and Industry runs May 1 through early 2027. Music of Remembrance's opera commission "The Dialogue of Memories" is at the Studebaker Theater, May 23–24. The opera with a libretto by Howard Reich with Tom Cipullo was inspired by former Chicago Tribune critic Reich's 2019 book with the late Elie Wiesel.
In September, I saw Chicago Opera Theater's workshop production of Aaron Israel Levin's "Trusted" about a financial scandal, so I'm anxious to see how the work has developed when I see "Trusted: Concert World Premiere" at the Studebaker Theater on May 30. Singer-songwriter Natalie Merchant, the Chicago Children's Theatre and the Negaunee Music Institute at the Chicago Symphony Orchestra (CSO) present "Mother Goose & The Cabinet of Wonder," a singalong concert, part of the CSO for Kids series, on May 9 at 11 a.m. and 12:45 p.m. at Symphony Center. In July, the CSO moves outdoors to Ravinia to begin its 90th residency there.
As part of its indoor salon series, Glessner House hosts "La Belle Époque" on May 17 featuring Andrea Baker, soprano, Evan Bravos, baritone, accompanied by pianist Nicholas Pothier. Its first outdoor jazz concert of the season is "Courtyard Concert: Elaine Dame" on May 27 featuring singer Elaine Dame with pianist Jeremy Kahn. A group of preservationists intent on saving the Glessner House bought it sixty years ago. The organization founded by that group would become what is now the Chicago Architecture Center. Today Glessner House is a house museum and its own non-profit corporation.
In American politics, a "smoke-filled room" is a place where powerful stogie-smoking politicians pull the strings behind the scenes. The original "smoke-filled room" was in the Blackstone Hotel (1908). It, along with the Blackstone Theatre (1910) next door, were designed by the prominent architectural firm of Marshall and Fox. The Blackstone Theatre became DePaul University's Merle Reskin Theatre and hosted the university's theater and music performances for more than thirty years. DePaul will close the theatre and move operations to the Lincoln Park campus after the theatre's last scheduled show "Mirror of Most Value: A Ms. Marvel Play," which runs May 14–30. I saw Katherine Hepburn and Christopher Reeve perform in Enid Bagnold's "A Matter of Gravity" at the Blackstone in 1977.
The Glessner House and the closing of the landmarked Beaux Art Blackstone Theater reminds me that May is National Preservation Month. The Wright Plus℠ Architectural Housewalk in Oak Park on May 16 is a hybrid event of sorts — you can admire the exteriors of eight beautifully preserved private homes designed by Frank Lloyd Wright and his contemporaries and, in addition, tour their interiors.
TimeLine Theatre has a new home at 5035 North Broadway. The inaugural production there is Amy Herzog's adaptation of Henrik Ibsen's "An Enemy of the People," May 6–June 7. Remy Bumppo Theatre Company introduces audiences to both new and older plays with Readings on Ravenswood on Mondays, May 4–June 15. The weekly event includes post-reading discussions about the plays.
May is your chance to see a movie outdoors! The 5th season of the Rooftop Cinema Club's screenings starts May 6 on the 5th floor terrace of Emily Hotel.
Festivals also migrate from indoors to the outdoors this month. The Chicago Humanities Festival's Lakeview Day is on May 9. Just a few of the offerings include a presentation by author and Emmy Award-nominated TV host Padma Lakshmi and "David Axelrod and David French in Conversation" at the Athenaeum Center. It should be a very lively conversation between liberal political commentator Axelrod and conservative New York Times columnist French. The Chicago Humanities Festival's Northwestern University Day in Evanston on May 17 includes presentations by chef Curtis Duffy, filmmaker John Waters and the three great-nieces of Frida Kahlo.
The first outdoor farmers markets, and food and music festivals open this month. The indoor season of the Wicker Park Farmers Market ended March 29. The market moves outdoors to 1425 North Damen on Sundays, May 3–October 25. May 21 is the first Daley Plaza City Market (Thursdays) which is Chicago's longest running farmers' market.
Chicago's hot dogs are so iconic that there was a hot dog vendor with a pushcart at last month's EXPO Chicago. One of summer's most popular food fests is the Windy City Hot Dog Fest on May 29–31 at Six Corners in Portage Park. Likewise, the Do Division Street Fest, May 29–31, is often featured on Chicago's "best fests" list.
Tickets go on sale to the public on May 6 to the Obama Presidential Center, which opens on June 19 and features the works of local artists such as Richard Hunt. The late sculptor Hunt was the first artist commissioned by the Obama Foundation to create a piece of art for the center.
Dates, times, locations and availability are subject to change.
Photo Credits: Lyric Opera of Chicago; Music Institute of Chicago; Anti-Cruelty; Mandala South Asian Performing Arts; Chicago Opera Theater; Joe Mazza / brave lux, inc.; Wicker Park & Bucktown Chamber of Commerce.
