
#1 Theater, Dance & Music Event
This year, the esteemed ball celebrated the close of the symphony's 125th anniversary season. With 600 guests—an increase from 500 in 2015—the evening kicked off with a cocktail reception followed by a program that recreated the symphony's first-ever concert on October 16, 1891. Afterward, guests headed to a gala celebration at the nearby Palmer House Hilton, and partook in cocktails, dinner, and dancing in the hotel's famous Red Lacquer Room. The night raised $1.5 million. Next: Fall 2017

#3 Theater, Dance & Music Event
More than 600 guests attended the benefit, which started with a cocktail reception at Steppenwolf’s new in-theater bar and coffee shop, Front Bar. The evening also included a performance followed by a live auction, dinner, and dancing in a tent that spanned the theater’s parking lot. The event raised $1.3 million. Next: Spring 2017

#4 Theater, Dance & Music Event (up from #5)
The gala celebrated its 50th anniversary with a performance from the Chicago Symphony Orchestra, conducted by James Levine. While 650 guests attended last year, this year’s gala drew some 700 attendees. It raised more than $1 million, which was on a par with the money raised last year. Event Creative’s decor included 9-foot, color-changing chandeliers. Next: July 2017

#5 Theater, Dance & Music Event
This year’s gala honored the ballet company’s 60th anniversary. The evening began with a special performance at the Auditorium Theatre. Afterward, guests boarded trolleys and headed to a dinner-dance at the Hilton Chicago, where young dancers from the ballet’s Community Engagement program performed. Some 700 guests attended, including Mayor Rahm Emanuel. The gala raised more than $1 million. Next: Spring 2017

#6 Theater, Dance & Music Event (up from #8)
Marking the 400th anniversary of Shakespeare’s death, this year’s gala raised a record $1.4 million. It drew 500 guests, as compared to 350 guests in 2015. Held at Navy Pier, the evening featured a performance from actor Alan Cumming. It culminated in a fireworks show set to live music from the Chicago Symphony Orchestra. Next: Spring 2017

#7 Theater, Dance & Music Event
Held at the Fairmont Chicago, this year’s black-tie affair featured a performance from Broadway star and Scandal actor Norm Lewis, who sang show tunes. Some 500 guests attended the gala, which raised more than $850,000 for the theater. Next: May 2017

#8 Theater, Dance & Music Event
Billed as the nation’s largest dance festival, the event celebrated its 10th anniversary this year. The fest—held at indoor and outdoor venues throughout the city—featured 25 free performances. New programming included a world-themed showcase at Navy Pier called “Planet Chicago.” Next: Summer 2017

#9 Theater, Dance & Music Event
The Chicago Children’s Choir feted its 60th anniversary at this year’s gala, which took place at the Geraghty. Some 750 guests attended this year, which marks a boost over the 600-guest attendance in 2015. The night featured a performance from choir alum and Broadway star Allison Semmes. Next: Fall 2017

#10 Theater, Dance & Music Event (up from #12)
The local theater company gave its gala a “Vaudeville” theme this year. Some 370 guests attended, raising $825,000, an increase from 2015’s take of $700,000. The benefit also took place at a new venue: Revel Fulton Market. Next: Spring 2017

#11 Theater, Dance & Music Event (up from #13)
The ball always has an elaborate theme, and this year’s was “Dragstrip.” Some 400 guests attended the benefit for the L.G.B.T. theater company, and the event brought in $75,000, an increase from $60,000 in 2015. Event highlights included a custom beauty and wig shop, a punch-out prize wall, and performances from local drag performers. Next: Spring 2017

#12 Theater, Dance & Music Event
Some 450 guests attended the ball, which raised more than $800,000. More than $225,000 of the total was raised the night of the event, with help from a live auction and paddle raise. The evening also included a performance at the Harris Theater, followed by a dinner-dance at the Radisson Blu Aqua Hotel. Next: Spring 2017

#13 Theater, Dance & Music Event
This year’s event drew some 230 guests to the Chicago History Museum. The evening included an awards presentation, and raised $110,000 to support the programming at 240 member theater companies. Next: Spring 2017