1. Joffrey Ballet Spring Gala

Up from #6
This year, organizers parted with the event’s traditional format to deliver something totally fresh. Instead of a sit-down dinner, the revamped gala, dubbed the UNgala, offered food stations dispersed throughout multiple levels of the Lyric Opera House (a new venue for the event.) Entertainment, also new, varied from drag queen performances to magic tricks and impromptu dance performances from Joffrey stars. The splashy affair drew some 800 guests, as compared to 700 in 2018. The fashionable crowd represented a diverse age range, including the coveted Millennial bracket. UNgala raised more than $1.4 million, which marks a significant increase from the 2018 take of approximately $1 million. Next: April 17, 2020
See more: This Is What Happens When You Turn a Traditional Annual Gala Into an 'UNgala'
This year, organizers parted with the event’s traditional format to deliver something totally fresh. Instead of a sit-down dinner, the revamped gala, dubbed the UNgala, offered food stations dispersed throughout multiple levels of the Lyric Opera House (a new venue for the event.) Entertainment, also new, varied from drag queen performances to magic tricks and impromptu dance performances from Joffrey stars. The splashy affair drew some 800 guests, as compared to 700 in 2018. The fashionable crowd represented a diverse age range, including the coveted Millennial bracket. UNgala raised more than $1.4 million, which marks a significant increase from the 2018 take of approximately $1 million. Next: April 17, 2020
See more: This Is What Happens When You Turn a Traditional Annual Gala Into an 'UNgala'
Photo: Vin Reed
2. Lyric Opera of Chicago's Opening Night Gala Benefit and Opera Ball

This year’s gala benefit and opera ball began with a lavish ceremony at the Lyric Opera, where the company’s stars walked a red carpet and operagoers sipped champagne before a production of Rossini’s Barber of Seville. Afterwards, some 400 guests hopped trolleys to the Hilton Chicago for a late-night ball, which featured grand elements including a trumpeted procession of opera stars and co-chairs. At the dinner-dance, the theme of Seville came to life via tiled bars, mock lemon trees, and a Spanish-inspired menu. Organizers did not disclose the fund-raising total. Next year, the opera will reinvent its season-opener event in a new format that’s yet to be announced. Next: Fall 2020
Photo: Robert Kusel
3. Chicago Symphony Orchestra's Symphony Ball

Romeo and Juliet set the tone for this year’s ball, which began with a symphony concert that included Tchaikovsky’s classic score. Afterward, some 500 guests boarded trolleys to head to a dinner-dance at the Four Seasons Chicago. Actors wearing Renaissance-style garb and props including a Juliet balcony helped channel the theme at the lavish reception, where guests sipped champagne rimmed in golden sugar. The evening raised almost $1.5 million. Next: October 3, 2020
Photo: Courtesy of Chicago Symphony Orchestra
4. Ravinia Festival Gala

Chicago native Jennifer Hudson was the vocalist at this year’s gala, and she delivered a powerhouse performance alongside the Chicago Symphony Orchestra. The evening also included cocktails on the outdoor music venue’s North Lawn, and a tented dinner following the show. Attended by 800 guests, the event raised $1.1 million, as compared to just short of $1 million in 2018. Next: Summer 2020
See more: See a Black-Tie Gala Inspired by Megawatt Performer Jennifer Hudson
See more: See a Black-Tie Gala Inspired by Megawatt Performer Jennifer Hudson
Photo: Courtesy of Ravinia
5. Chicago Children's Choir's Red Jacket Optional Gala

Up from #9
In 2018, the hip event drew more than 600 guests and raked in $1.37 million (compared to $1.25 in 2017). Held at the Geraghty, the evening included live and silent auctions, live music, and dinner. The after-party featured music from Pitch Mafia, which features Chicago Children’s Choir alumni. Two of Chicago’s cult-followed eateries—Big Star Taco and Hoosier Mama pies—contributed late-night bites. Next: October 18, 2019
In 2018, the hip event drew more than 600 guests and raked in $1.37 million (compared to $1.25 in 2017). Held at the Geraghty, the evening included live and silent auctions, live music, and dinner. The after-party featured music from Pitch Mafia, which features Chicago Children’s Choir alumni. Two of Chicago’s cult-followed eateries—Big Star Taco and Hoosier Mama pies—contributed late-night bites. Next: October 18, 2019
Photo: Todd Rosenberg Photography
6. Steppenwolf Theatre Gala

This year’s fund-raiser drew some 600 guests, including Chicago’s newly elected mayor Lori Lightfoot. Armie Hammer served as the evening’s M.C., while another big-name actor, James Franco, was the guest auctioneer. Held at Rockwell on the River for the first time, the event raised about $1.27 million. Next: Spring 2020
Photo: Kyle Flubacker
7. Chicago Shakespeare Theater Gala

The 2019 gala, held on Navy Pier, raised $1.2 million. Highlights of the event included a one-night-only musical performance from the cast of Six, which was then enjoying a successful run at the Chicago Shakespeare Theater. The 350 attendees also had the chance to snap photos with performers dressed in lavish Shakespearean costumes. Next: Spring 2020
Photo: Michael Litchfield
8. Goodman Theatre Gala

Singer Megan Hilty was the performer at this year’s gala, which returned to the Fairmont Chicago. Some 650 guests attended the black-tie benefit, helping to raise more than $800,000. Kehoe Designs provided decor, decking the ballroom in chandeliers and purple flowers. Next: May 16, 2020
Photo: John Reilly Photography
9. Lookingglass Theatre Company's Gglassquerade

Offering cocktails, dinner, dancing, and live and silent auctions, the gala took place at the University Club of Chicago. The 314 guests included boldface names like Mayor Lori Lightfoot and celebrity chef Rick Bayless. The event raised $900,000 and featured musical performances from the theater’s productions. Next: Spring 2020
Photo: Mark Campbell Photography
10. Dance For Life

Dance for Life showcases performances from several Chicago dance companies, who come together for one evening to raise money for local dancers affected by critical health issues. In 2019, the event had its all-time highest attendance with 3,100 guests. It also raised record-breaking funds by bringing in $300,000. Next: Summer 2020
Photo: Todd Rosenberg
11. Hubbard Street Dance Company's Spotlight Ball

This year’s event, held at the Harris Theater for Music and Dance, raised some $500,000 for the prestigious dance company’s programming. More than $200,000 of that total was raised the evening of the gala, when a high-spirited paddle raise took place. The event drew 300 guests, and included a performance in addition to cocktails and dinner. Next: May 15, 2020
Photo: Stacey Rupolo
12. About Face Theatre's Wonka Ball

With a “Disco Inferno” theme, this year’s event drew some 300 guests and raised $65,000. Along with a presentation of the Leppen Leadership Awards, the evening featured cocktails, spirited live entertainment, and dancing to disco music. Many guests opted to don costumes, arriving in polyester suits, platform shoes, and wild wigs. Next: Spring 2020
Photo: Timmy Samuel
13. League of Chicago Theatres Gala

The league, which celebrated its 40th anniversary in 2019, hosted its annual gala at the Palmer House Hilton. Some 220 industry pros gathered at the networking event, which raised $125,000 of funding for local theater companies. The evening also celebrated the winner of the Broadway in Chicago Emerging Theatre Award, the Interrobang Theatre Project. Next: Spring 2020
Photo: Violetta Photo